Title of Invention	"AN ESTER OF FORMULA (I), AS PRECURSOR OF FRAGRANT ALCOHOL OR KETONE OR ALDEHYDE"
Abstract	"{_A process for the preparation of a compound of formula (1)wherein Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical and R represents a group of formulawherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formulaor R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from an fragrant ketone of formulaand, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted, which process comprises reacting an aldehyde of formula R2CHO, or a ketone of formula R2 R^O, R1 and R2 being defined as above, with acetic anhydride to obtain a compound of formula R2R1 COCOCH3, and subjecting the latter to a reaction with YCOC1, Y being defined as above. In the presence of potassium tert-butoxide, to obtain a compound of formula YCOOCR2R1.

Title of Invention

"AN ESTER OF FORMULA (I), AS PRECURSOR OF FRAGRANT ALCOHOL OR KETONE OR ALDEHYDE"

Abstract

"{_A process for the preparation of a compound of formula (1)wherein Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical and R represents a group of formulawherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formulaor R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from an fragrant ketone of formulaand, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted, which process comprises reacting an aldehyde of formula R2CHO, or a ketone of formula R2 R^O, R1 and R2 being defined as above, with acetic anhydride to obtain a compound of formula R2R1 COCOCH3, and subjecting the latter to a reaction with YCOC1, Y being defined as above. In the presence of potassium tert-butoxide, to obtain a compound of formula YCOOCR2R1.

Full Text	The present application is divisional of Indian Patent Application No. 191/DEL/1995. The present invention relates to an ester of formula (I) as precursor of fragrant alcohal or ketone or aldehyde. The present invention- relates to the field of perfumery and, mon particularly, to improved perfumed detergents and fabric softeners. The use of enzymes in fabric detergents, in order to improve theii efficiency/ has been known for a number of years. Amongst said enzymes, lipases are particularly preferred, as a result of their capacity to hydrolyse the fat materials on the dirty linen and thus to facilitate its cleaning. However, it is known that xnalodour problems can occasionally occur under certain application conditions. In order to solve these malodour problems, there has been proposed a method (see for example EP 430 315) consisting in carefully choosing the perfuming ingredients incorporated in the detergents and which, following the washing, are deposited on the fabrics. Therefore, appropriate perfuming of said detergents appears to be extremely important. On the other hand, it would be desirable that said detergents and fabric softeners are able to impart to the fabrics a long-lasting odour, such that the user perceives this odour even a long time after the textiles have been washed and subsequently dried. To this end, it has been known, to use in the fabric detergents and softeners perfuming ingredients which have a good tenacity on the fabrics, i.e. ingredients whose odour, once imparted to the textiles upon the washing, can then be perceived hy the consumer for several days. However, there are many perfuining substances .known for their extremely pleasant odours, and namely a quality of "freshness" often associated with the notion of cleanliness, which substances are unfortunately not very tenacious, or even not tenacious at all, on fabrics, such that their perfuming effect can only be perceived very briefly, at the most for a few hours following the washing and drying operations. Clearly, prolonging the fragrance effect of such substances, and thus the "freshness" of the fabrics, would be highly desirable. The present invention brings precisely a novel solution to this problem. We have now unexpectedly discovered a better process for perfuining textiles washed -with detergents containing lipases. We have in fact been able to establish that, by adding particular ingredients to the fabric detergent and/or to the fabric softener that is subsequently applied, one could distinctly improve the odour of the fabrics treated with theseproducts and prolong in a remarkable way the fragrance of said fabrics after drying. A first object of the present invention is thus to provide a process for perfuming fabrics washed in the presence of a Kpase-containing detergent and, optionally, subsequently treated with a fabric softener, said process being characterized in that said detergent and/or said fabric softener contains a compound of formula (Formula Removed) wherein a. R represents a radical derived from a fragrant alcohol of formula ROH and Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical, or a -(CH2)nCOOR group wherein R is defined as above and n is an integer from 0 to 6 ; or b. Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical and R represents a group of formula wherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formula (Formula Removed) or R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from a fragrant ketone of formula and, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted. By an alkylidene radical derived from a fragrant aldehyde or ketone, it is understood here a radical which, upon the conversion of enol-ester (I) into said aldehyde or ketone, regenerates the corresponding R group which is the substituent of said aldehyde or ketone. Thus, for example, when the fragrant aldehyde is 3,7-dimethyl-6-octenal (R is 3,7-dimethyl~6-octenyl), the corresponding alkylidene radical in enol-ester (I) is 3,7-dimethyl-l,6-octadienyl. According to a variant of the invention, there is provided a process for perfuming fabrics washed in the presence of a lipase-containing detergent, which process comprises the treatment of said fabrics, after the washing cycle, with a fabric softener containing a compound of formula (I) as defined above. By "fragrant alcohol", "fragrant aldehyde" or "fragrant ketone" it is meant here any alcohol, aldehyde, respectively ketone, of current use in perfumery, which is capable of imgajrjting an odour to fabrics or textiles,^ upon the process of washing and/or the treatment with a fabric softener. We have in fact discovered that the perfuming effect of such compounds could be remarkably improved, and namely their diffusion prolonged, if they were replaced by the corresponding compound (I) in the detergent or fabrt softener used. This result is all the more surprising in that the compounds (I) are themselves either devoid of odour, or they possess weak and characterless odours, and are thus apparently useless for perfumery. Yet, when used according to the invention, they are not only capable of imparting to the fabrics the characteristic odour of the corresponding alcohol, aldehyde or ketone, but also of prolonging their effect of diffusion, such that said odour develops itself for much longer periods of time than in the case where said corresponding alcohol, aldehyde or ketone is directly added to the detergents or fabric softeners. Therefore, the use of compounds (I) according to the process of the invention is translated into an enhanced"1 substantivity of the corresponding alcohols, aldehydes and ketones. The advantages of this process are all the more obvious in the case of the numerous odoriferous alcohols which are known to be weakly tenacious on washed fabrics and the odour of which, although distinctly perceived when the fabrics are removed from the washing machine, does not remain on the linen and can no longer be perceived after 12 to 24 h. Many examples of such alcohols can be found in the prior art, some of which only contribute to the odour of the fabrics for a very short time, and no doubt many others will be discovered in the future. For all these alcohols, the process according to the invention makes it possible to remarkably improve their odoriferous performance on fabrics, by prolonging the diffusion time of their characteristic notes and thus the time during which they contribute significantly to the overall odour. We have in fact established that the use of the corresponding compounds (I) in the detergents and/or fabric softeners made it possible to obtain a perfuming effect equivalent to the one that would have been observed with the prolonged diffusion ("slow-release") of the alcohol, if such a diffusion would have been possible, which is not the case in practice. Quite clearly, it is impossible to list in an exhaustive manner all the alcohols of formula ROH known to this day, which are capable of imparting pleasant odours to the textiles treated with the laundry products perfumed by way of said alcohols, and the perfuming effect of which can be remarkably improved according to the invention. However, by way of example, one can cite alcohols such as anisic alcohol, cinnamic alcohol, fenchylic alcohol, 9-decen-l-ol, phenethylol, citronellol, 3-methyl-5-phenyl-1-pentanol (origin : Firmenich SA, Geneva, Switzerland), Mayol ® (7-p-menthan-1-ol ; origin : Firmenich SA, Geneva, Switzerland), dihydromyrcenol (2,6-dimethyl-7~octen-2-ol), geraniol (3,7-dimethyl-2,6~ octadien-1-ol), (Z)-3-hexen-l-ol, 1-hexanol, 2-hexanol, 5-ethyl-2-nonanol, 2,6-nonadien-l-ol, borneol, l-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol (origin : Firmenich SA, Geneva, Switzerland), 2-methyl-4-phenyl-2-butanol, 2-methyl-l-phenyl-2-propanol, cyclomethylcitronellol, decanol, dihydroeugenol, 8-p-menthanol, 3,7-dimethyl-l-octanol, 2,6-dimethyl-2-heptanol, dodecanol, eucalyptol, eugenol, Florol ® (tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol; origin : Firmenich SA, Geneva, Switzerland), isoeugenol, linalol, Tarragol ® (2-methoxy-4-propyl-l-cylohexanol; origin : Firmenich SA, Geneva, Switzerland), terpineol, tetrahydromuguol, 3,7-dimethyl-3-octanol and Lyral ® (3 and 4-(4-hydroxy-4-methylpentyl)~ cyclohex-3-ene-l-carbaldehyde ; origin : International Flavors and Fragrances, USA). It is quite obvious, however, that the process of the invention is perfectly general and can relate to many other alcohols which the skilled person is quite able to choose from the general knowledge in the art and as a function of the olfactive effect it desires to achieve. Analogous considerations apply to the aldehydes of formula (Formula Removed) and to the ketones of formula (Formula Removed) The process of the invention is advantageous whenever the compounds such as those mentioned above show a weak tenacity on fabrics, and there are many odoriferous aldehydes and ketones whose performance on textiles turns out to be disctinctly improved when these compounds exert their perfuming activity by way of the corresponding enol-esters of formula (I). Again, although one cannot cite in an exhaustive manner all the fragrant aldehydes and ketones which can be used according to the process of the invention, there can be cited, by way of example, compounds such as C6 to C12 aldehydes, hydratropic aldehyde, methyl nonyl acetaldehyde, phenylpropanoic aldehyde, Acropal ® [3- or 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde ; origin : Givaudan-Roure, Vernier, Switzerland], 2-methyldecanal, 4-isopropyl-l-benzeneacetaldehyde, (4-methyl-l-phenyl)acetaldehyde, Z-6-nonenal, citral, citronellal, 9-decenal, 3-(4-isopropyl-l-phenyl)-2-methylpropanal (origin : Firmenich SA, Geneva, Switzerland), (E,E)-2,4-heptadienal, (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal, 5,9-dimethyl-4,9-decadienaI, (Z)-6-octenal, Farenal ® (2,6,10-trimethyl-9-undecenal; origin : Givaudan-Roure, Vernier, Switzerland), Foliaver ® [3-(4-methoxy-l~phenyl)-2-methylpropanal ; origin : International Flavors and Fragrances, USA], Heliopropanal ® [3-(l,3-benzodioxol-5-yl)-2-methylpropanal; origin : International Flavors and Fragrances, USA], (Z)-4-heptenal, le 3,5,5-trimerhylhexanal (origin : International Flavors and Fragrances, USA), (4-methyl-l-phenoxy)acetaldehyde, hydroxycitronellal, isocyclocitral (origin : International Flavors and Fragrances, USA), Lilial ® [3-(4-tert-butyl-l-phenyl)-2-methylpropanal ; origin : Givaudan-Roure, Vernier, Switzerland], le l-p-menthene-9-carbaldehyde (origin : Firmenich SA, Geneva, Switzerland), Lyral ® [3- and 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde ; origin : International Flavors and Fragrances, USA], 2,6-dimethyl-5-heptenal, l-p-menthen-9-al, (E)-2-octenal, (2E,6Z)-2,6- nonadienal, 3-methyl-5-phenylpentanal, (E)-4-decenal, (E)-2-undecenal, 3,7-dimethyloctanal, Zestover (2,4-dimethyl-3-cyclohexene-l-carbaldehyde; origin : Firmenich SA, Geneva, Switzerland), 3-phenylbutanal, Scentenal ® (octahydro-5-methoxy-4,7-methano-lH-indene-2-carboxaldehyde ; origin : Firmenich SA, Geneva, Switzerland), 2,5,9-trimethyl-4,9-decadienal, Intreleven aldehyde (undecenal ; origin : International Flavors and Fragrances, USA), 4-methyl-phenyl-propanoic aldehyde, 4-(4-hydroxy-l-phenyl)-2-butanone, benzylacetone, the ionones, 3-(4-tert-butyl-l-phenyl)propanal, carvone, 3,7-dimethyl-l,l-bis(ll-methyldodecyloxy)-2,6-octadiene, muscone, 2-pentyl-l-cyclopentanone, l'ethyl amyl ketone, l'ethyl pentyl ketone, la 2-heptyl-l-cyclopentanone, geranylacetone, Iralia ® (methylionone ; origin : Firmenich SA, Geneva, Switzerland), Iso E super [l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone ; origin : International Flavors and Fragrances, USAl, 6-methyl-5-hepten-2-one, methyl jasmonate, methyl hexyl ketone, methyl pentyl ketone, methylnonyl ketone, cis-jasmone, Hedione ® (methyl dihydrojasmonate ; origin : Firmenich SA, Geneva, Switzerland), civettone, 4-(l,l-dimethylpropyl)-l-cyclohexanone, Exaltone ® (cyclopentadecanone ; origin : Firmenich SA, Geneva, Switzerland), 2,6,6-trimethyl-2-cyclohexene-l,4-dione, p-tert-butylcyclohexanone, tricyclo[6.2.1,02'7]undec-9-en-3-one (origin : Firmenich SA, Geneva, Switzerland), 10,10-dimethyl-tricyclo[7.1.1.02'7]undec-2-en-4-one (origin : Firmenich SA, Geneva, Switzerland), Vertofix coeur (origine : International Flavors and Fragrances, USA), la perhydro-5,5,8a-trimethyl-2-naphtalenone (origin : Firmenich SA, Geneva, Switzerland) or 5-methyl-exo-tricyclo[6.2.1.02'7]undecan-4-one. Furthermore, it should be noted that the process of the invention is of much more general use than merely the improved perfuming of textiles treated with laundry products containing lipases. It constitutes, in fact, a general process for washing said textiles which is also advantageous whenever it is desired to improve the activity of certain agents, fragrant or other, currently present in laundry products, i.e. detergents and fabric softeners. It is well-known for instance that said laundry products are often very aggressive media, wherein a great number of perfuming ingredients, and more particularly fragrant aldehydes, turn out to be unstable and cannot therefore be used to perfume those products, nor the textiles washed therewith. The use according to the invention of the corresponding esters and enol-esters of formula (I) can obviate this problem whenever said enol- esters turn out to be more stable. It is also quite clear that one can make use of the process of the invention to improve and prolong the action of bactericide agents, namely alcohols, whether they are fragrant or not. Therefore, the process according to the invention is in fact a general process for treating textiles or fabrics upon the washing of the latter with a lipase-containing detergent, which washing can be followed by treatment with a fabric softener, according to which process any alcohol, aldehyde or ketone currently used in fabric detergents or softeners for its perfuming, bactericide or other activity, can be replaced by the corresponding compound (I), so as to improve its activity. Compounds (I) are novel chemical entities and thus are also the object of the invention. Amongst said compounds, those wherein y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical are fatty acids esters or enol-esters which do not themselves possess an interesting odour, but which, when used according to the process of the invention, are capable of imparting to the fabrics the fragrances typical of the corresponding alcohols, aldehydes and ketones defined above. Said compounds, in particular the derivatives having 12 to 16 carbon atoms, are preferred according to the invention, owing to the particularly advantageous results obtained upon their use. As regards the compounds (I) wherein Y represents a -(CH2)nCOOR group, R being defined as above and n being an integer from 0 to 6, they are novel diesters, which are either devoid of odour, or possess odours which are not particularly useful for perfumery. However, they showed similar behaviour to that of the compounds (I) cited here-above, when used in the context of the present invention. The compounds (I) of the invention can be added to the detergents and fabric softeners either on their own, or in admixture with other perfuming ingredients, solvents or adjuvants, of current use in perfumery. The concentrations in which they can be added to the detergents and fabric softeners according to the invention have the values usual in the art for this type of products. The skilled person is quite able to select such values as a function of the nature of the product to be perfumed and of the desired olfactive effect. By way of example, concentrations of the order of 0.01 to 1%, or even up to 5%, by weight of compound (I), relative to the weight of detergent or fabric softener composition, can be cited. The fabric detergents and softeners according to the invention can take the form of powders or granular solids, bars, pastes or yet aqueous or non-aqueous liquids, and contain the usual ingredients for this type of product. Thus, the detergents can typically contain, in addition to the lipase (see, for example, EP 430 315 for a detailed description of the type of lipases that can be used according to the present invention), for example active anionic, cationic, zwitterionic or non-ionic compounds, as well as filling agents, bleaching agents, confining agents and other ingredients of current use in the detergent bases intended for washing linen. A detailed description of the base detergent compositions which are adapted to be used according to the process of the invention is unwarranted here. A great many examples of such compositions can be found in the art and namely in the literature which is cited for instance in the European patent application mentioned above, or yet in European patent application EP 397 245. By way of example, a base detergent of this type, to which there is added the lipase in the desired concentration, can have the following composition (origin : Henkel KGaA, Diisseldorf, Germany) : Ingredients % by weight Linear sodium alkyl benzene sulfonate (average length of the alcane chain :~Cn 5) 8.0 Ethoxylated tallow alcohol (14 EO) 2.9 Sodium soap (chain length C12_i6 : 13-26% C18-22 : 74-87%) 3.5 Sodium triphosphate 43.8 Sodium silicate (Si02 : Na20=3.3:l) 7.5 Magnesium silicate 1.9 Carboxymethylcellulose 1.2 Sodium ethylenediaminetetraacetate 0.2 Sodium sulfate 21.2 Water - 9.8 Total 100.0 Similar considerations apply to the fabric softener bases according to the invention, which will typically contain cationic softening ingredients of the type cited in EP 397 245 or in the literature mentioned in this reference. The compounds of the invention can be prepared by conventional synthetic methods. For example, the derivatives of fragrant alcohols were prepared by the esterification method summarized in the following reaction scheme : Scheme I (Scheme Removed) wherein Y and R are defined as in claim 1. The enol-esters of fragrant aldehydes and ketones were also prepared by conventional methods, starting from said aldehydes and ketones, by way of reactions of the type of those represented hereinafter : (Formula Removed) R1, R2 and Y are defined as in claim lb. a) acetic anhydride ; potassium acetate; e thyl amine ; 120°; see, for example, D.P. Simmons et al., Helv. Chim. Acta 71, 1000 (1988) a') acetic anhydride; p-toluenesulfonic acid (cat.); 120° ; see, for example, T. Taapken et al., J. Chem. Soc. Perkin Trans. 1,1994. 1439 b) potassium tert-butoxyde; YCOC1 ; see, for example, P. Duhamel et al., J. Chem. Soc. Perkin Trans. I, 1993. 2509 The reaction conditions are described in detail in the preparation examples presented hereinafter, wherein the temperatures are in degrees centigrade and the abbreviations have the usual meaning in the art. The invention will also be illustrated by way of application examples. Example 1 Preparation of mono-esters General me trio d To a stirred solution of the appropriate ROH alcohol (0.064 mole) and triethylamine (7.4 g, 0.073 mole) in CH2C12 (HO ml), there was added dropwise during 20 min, at 15° and under N2 the corresponding YC(0)C1 acyl chloride (0.07 mole), wherein Y is a C7 to C24, linear of branched, saturated or unsaturated alky] radical. After 2 h at room temperature, the mixture was poured on aq. sat. NaHCO3 (excess) and the organic phase was separated. Extraction of the aqueous phase with CHL2C12 was followed by washing of the combined organic phases with 10% aqueous NaCl. The reaction product was dried over Na2SO4, concentrated and distilled to provide the desired ester in a pure state and in 80 to 90% yield. The following mono-esters were prepared according to the above-described general method. a. 2-phenylethyl octanoate B. p. 100-101°/4Pa rR(CHCl3) : 2930, 2858, 1728, 1498, 1455, 1168, 1106 cm-l NMR(1H, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.27(8H) ; 1.59(2H) ; 2.28(t, J=7Hz, 2H) ; 2.93(t, J=7Hz, 2H) ; 4.29(t, J=7Hz, 2H) 7.20-7.35(5H) 5 ppm. NMR(13C) : 173.7(s) ; 138.0(s) ; 128.9(d) ; 128.5(d) ; 126.5(d) ; 64.7(t) ; 35.2(t); 34.4(t); 31.7(t) ; 29.1(t); 28.9(f); 25.0(f); 22.6(f); 14.0(q) 5 ppm. MS : 248(0, M+), 127(2), 104(100), 57(12). b. 2-phenylethyl hexadecanoate M. p. 40° IR(CHCl3) : 2927, 2855, 1728, 1456, 1174 cm-1 NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.26(24H) ; 1.58(2H) ; 2.27(t, J=7Hz, 2H) ; 2.93(t, J=7Hz, 2H) ; 4.29(t, J=7Hz, 2H) ; 7.20-7.35(5H) 8 ppm. NMR(13C): 173.7(s); 138.0(s) ; 128.9(d); 128.5(d); 126.5(d); 64.7(t) ; 35.3(f) ; 34.4(t) ; 32.0(t) ; 29.7(2t) ; 29.5(t) ; 29.4(t) ; 29.3(f) ; 29.2(t) ; 25.0(t) ; 22.7(t) ; 14.1(q) 5 ppm. MS : 360(0, M+), 104(100). c 3,7-dimethyl-6-octenyl octanoate B. p. 108-109°/2.7Pa IR(CHCl3) : 2829, 2858, 1725, 1460, 1379, 1231, 1171, 1106 cm"1 NMR(1H, 360MHz): 0.88(t, J=7Hz, 3H) ; 0.91(d, J=7Hz, 3H) ; 1.10- 1.80(15H); 1.61(s, 3H) ; 1.68(s, 3H) ; 1.98(m, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.10(m, 2H) ; 5.09(broad t, J=7Hz, 1H) 5 ppm. NMR("C) : 173.9(s) ; 131.3(s) ; 124.7(d) ; 62.8(t) ; 37.1(t) ; 35.6(t) ; 34.5(t) ; 31.7(t) ; 29.6(d) ; 29.2(t) ; 29.0(t) ; 25.7(q) ; 25.5(t) ; 25.1(t); 22.6(1); 19.5(q) ; 17.7(q) ; 14.1 (q) 5 ppm. MS : 282(0, M+), 138(30), 123(56), 109(25), 95(77), 81(100), 69(59). d. 3,7-dimethyl-6-octenyl hexadecanoate B. p. (bulb-lo-bulb distillation) 210-230°/5.3 Pa IR(CHC13) : 2827, 2855,1725,1465,1233,1178 cm"1 NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 0.92(d, J=7Hz, 3H) ; 1.15- 1.35(26H); 1.44(m, 1H); 1.60(s, 3H) ; 1.68(s, 3H) ; 1.50-1.70(4H) ; 1.98(m, 2H); 2.28(t, J=7Hz, 2H) ; 4.10(m, 2H) ; 5.09(broad t, J=7Hz, 1H) 5 ppm. NMR(13C) : 173.9(s) ; 131.3(s) ; 124.6(d) ; 62.8(t) ; 37.1(t) ; 35.6(t) ; 34.5(t) ; 32.0(t) ; 29.7(2t) ; 29.6(d) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 25.7(q) ; 25.5(t) ; 25.1(t) ; 22.7(t) ; 19.5(q) ; 17.7(q) ; 14.1(q) 5 ppm. MS : 394(0, M+), 138(32), 123(30), 95(60), 82(70), 69(70), 57(100). e. 3-methyl-5-phenylpentyl octanoate B. p. 133-135°/2.7Pa IR(CHC13) : 2930, 2858, 1728, 1496, 1456,1231, 1171, 1106 cm" NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 0.98(d, J=7Hz, 3H) ; 1.28(8H) ; 1.40-1.80(7H) ; 2.27(t, J=7Hz, 2H) ; 2.62(m, 2H) ; 4.11(m, 2H); 7.10- 7.30(511) 5 ppm. NMR(!3C) : 173.9(s) ; 142.7(s) ; 128.3(2d) ; 125.7(d) ; 62.6(t) ; 38.8(t) ; 35.5(t) ; 34.4(t); 33.3(0; 31.7(0; 29.6(d); 29.2(0; 29.0(0; 25.0(0; 22.6(0; 19.5(q) ; 14.1(q) 5 ppm. MS : 304(0, M+), 160(55), 131(30), 104(100), 91(56). £. 3-methyl-5-phenylpentyl hexadecanoate B. p. (bulb-to-bulb distillation) 250°/4 Pa IRCCHCl3) : 2927, 2855,1727, 1456, 1235,1178 cm-1 NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 0.97(d, J=7Hz, 3tt) ; 1.26(24H) ; 1.48(2H) ; 1.55-1.80C5H) ; 2.27(t, J=7Hz, 2H) ; 2.62(m, 2H) ; 4.10(m, 2H) ; 7.15-7.30(5H) 5 ppm. NMR(13C) : 173.9(s) ; 142.6(s) ; 128.3(2d) ; 125.7(d) ; 62.6(t) ; 38.8(t) ; 35.5(t) ; 34.5(t) ; 33.3(t) ; 32.0(t) ; 29.7(2t) ; 29.7(d) ; 29.6(t) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t); 25.1(t) ; 22.7(t) ; 19.5(q) ; 14.1(q) 5 ppm. MS : 416(0, M+), 160(43), 129(22), 115(36), 104(72), 91(68), 71(61), 57(100). . 7-p-menthanyl octanoate (cis /trans 70:30) B. p. 105-115°/2.7Pa ER(CHC13) : 2929, 2858,1724,1453, 1232,1172,1106 cm-1 NMR(lH, 360MHz) : cis-7 : 0.86(d, J=7Hz, 6H) ; 0.88(t, J=7Hz, 6H) ; 2.30(t, J=7Hz, 2H) ; 4.02(d, J=7Hz, 2H) 8 ppm. trans-7 : 2.30(t, J=7Hz, 2H) ; 3.88(d, J=7Hz, 2H) 5 ppm. NMR(!3C) : cis-7 : 174.0(s) ; 66.6(t) ; 43.0(d) ; 34.5(t) ; 33.9(d) ; 30.6(d) ; 29.9(t) ; 29.2(t) ; 29.1(t) ; 26.5(t) ; 25.6(0 ; 25.1(t) ; 20.3(q) ; 14.0(q) 5 ppm. trans-7 : 174.0(s) ; 69.5(t) ; 44.1(d) ; 37.5(d) ; 32.9(d) ; 31.7(t) ; 22.6(t) ; 19.8(q) ; 14.0(q) 5 ppm. MS : cis-7 : 282(0, M+), 138(23), 123(17), 109(35), 95(100), 81(27). trans-7 : 282(0, M+), 138(27), 123(17), 109(22), 95(100), 81(35). . 9-decenyl octanoate B. p. 120-121O/2.7 Pa IR(CHC13) : 2830, 2857, 1725, 1466, 1171 cm-1 NMR(1H, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.30(18H); 1.61 (4H) ; 2.04(broad q, J=7Hz, 2H); 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=HHz, 1H) ; 4.99(broad d, J=17Hz, 1H) ; 5.80(m, 1H) 8 ppm. NMR(13C) : 173.9(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 33.8(t) ; 31.8(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 29.1(t) ; 29.0(2t) ; 28.8(t) ; 26.0(t) ; 25,l(t) ; 22.7(t) ; 14.1(q) 8 ppm. MS : 282(0, M+), 145(38), 109(38), 96(86), 82(89), 68(91), 55(100). 9-decenyl nonanoate B. p. (bulb-to-bulb distillation) 130-160°/2.7 Pa NMR(lH, 360MHz) : 0.88(1:, J=7Hz, 3H) ; 1.20-1.45(20H) ; 1-61 (4H) ; 2.04 (broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=llHz, 1H) ; 4.99(broad d, J=17Hz, 1H) ; 5.80(m, 1H) 5 ppm. NMR(«C) : 174.0(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 33.8(t) ; 31.9(t) ; 29.4(0 ; 29.3(t) ; 29.2(2t) ; 29.1(t) ; 29.0(t) ; 28.7(t) ; 26.0(t) ; 25.1(0 ; 22.7(t) ; 14.1(q) 5 ppm. MS : 296(0, M+), 159(27), 138(28), 96(100), 82(75), 68(73), 55(83). j. 9-decenyl decanoate B. p. 144-145°/2.7Pa IR(CHC13): 2929, 2856 1726,1466,1178 cm-1 NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H); 1.30(22H) ; 1.61(4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.05(t, J=7Hz, 2H) ; 4.93(broad d, J=llHz, 1H) ; 4.98(broad d, J=17Hz, 1H); 5.80(m, 1H) 5 ppm. NMR(13C) : 173.9(s) ; 139.1(d); 114.2(0 ; 64.4(0 ; 34.5(0 ; 33.8(0 ; 31.9(0 ; 29.5(0 ; 29.3(0 ; 29.2(t) ; 29.1(0 ; 29.0(0 ; 28.7(0 ; 26.0(0 ; 25.1(0 ; 22.7(0 ; 14.1 (q) 5 ppm. MS : 310(0, M+), 138(33), 109(29), 96(100), 82(82), 68(98). k. 9-decenyl undecanoate B. p. (bulb-to-bulb distillation) 130-150°/20 Pa NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.20-1.45(24H) ; 1.61(4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=llHz, 1H); 4.99(broad d, J=17Hz, 1H); 5.81(m, 1H) 5 ppm. NMR(13C) : 173.9(s) ; 139.1(d); 114.2(0 ; 64.4(0 ; 34.5(0 ; 33.8(0 ; 32.0(0 ; 29.6(20 ; 29.4(20 ; 29.3(0 ; 29.1(0 ; 29.0(0 ; 28.8(0 ; 26.0(0 ; 25.1(0 ; 22.7(t) ;14.1(q) 5 ppm. MS : 324(0, M+), 187(20), 138(43), 109(33), 96(100), 82(96), 68(89), 55(91). 1. 9-decenyl dodecanoate B. p. 164-165°/4Pa IR(CHCl3) : 2928, 2856, 1726, 1216 cm'1 NMR(lH, 360MHz) : 0.89(t, J=7Hz, 3H) ; 1.28(26H); 1.62(4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=HHz, 1H) ; 4.98(broad d, J=17Hz, 1H) ; 5.80(m, 1H) 5 ppm. NMR(13Q : 174.0(s) ; 139.2(d) ; 114.2(t); 64.4(t); 34.5(t) ; 33.8(t) ; 32.0(t) ; 29.6(t) ; 29.5(t) ; 29.4(2t) ; 29.3(t) ; 29.2(t) ; 29.1(2t) ; 28.9(t) ; 28.7(t) ; 26.0(t); 25.1 (t); 22.7(t); 14.1 (q) 5 ppm. MS : 338(0, M+), 138(48), 109(35), 96(100), 82(96), 68(89), 55(98). • 9-decenyl tridecanoate B. p. (bulb-to-bulb distillation) 150-175°/13 Fa NMR(1H, 360MHz): 0.88(t, J=7Hz, 3H) ; 1.20-1.45(28H) ; 1.61 (4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.05(t, J=THz, 2H); 4.93(broad d, J=HHz, 1H) ; 4.99(broad d, J=17Hz, 1H) ; 5.81(m, 1H) 5 ppm. NMR(13C) : 174.0(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 33.8(t) ; 32.0(t) ; 29.7(t) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 29.1(t) ; 29.0(t) ; 28.7(t) ; 26.0(t) ; 25.1(t) ; 22.7(t) ; 14.1(q) 5 ppm. MS : 352(0, M+), 138(52), 110(41), 96(99), 82(83), 68(93), 55(100). 9-decenyl t£tradecanoate B. p. (bulb-to-bulb distillation) 200-220°/4 Pa NMR(1H, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.28(30H) ; 1.62(4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=llHz, 1H); 4.99(broad d, J=17Hz, 1H) ; 5.81 (m, 1H) 5 ppm. NMR(13C : 174.0(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 34.5(t) ; 33.8(t) ; 32.0(t) ; 29.7(t) ; 29.5(t) ; 29.4(t) ; 29.3(2t); 29.1(t) ; 29.0(t) ; 28.7(t) ; 26.0(t) ; 25.1(t) ; 22.7(t) ; 14.1(q) 5 ppm. MS : 366(0, M+), 138(52), 110(47), 96(100), 82(96), 55(96). 9-decenyl pentadecanoate B. p. (bulb-to-bulb distillation) 175-210°/13 Pa NTMR(1H, 360MHz): 0.88(t, J=7Hz, 3H) ; 1.20-1.45(32H) ; 1.62(4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=llHz, 1H); 4.99(broad d, J=17Hz, 1H) ; 5.81(m, 1H) 5 ppm. NMR(13C) : 174.0(s) ; 139.1(d) ; 114.2(t); 64.4(t); 34.5(t) ; 33.8(t) ; 32.0(t) ; 29.7(2t) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 29.1(t) ; 29.0(t) ; 28.7(t) ; 26.0(t) ; 25.1(t) ; 22.7(t) ; 14.1 (q) 5 ppm. MS : 380(0, M+), 138(50), 110(30), 96(100), 82(85), 68(79), 55(80). p. 9-decenyl hexadecanoate NMR1H, 360MHz) : 5.84(111, 1H) ; 4.95(m, 2H) ; 4.05(t, 2H) ; 3.73(q, 4H) ; 2.31 (t, 2H) ; 2.05(broad q, 2H) ; 1.61(m, 4H); 1.2-1.4(broad m, 30H); 0.89(111, 3H) 5 ppm. NMR(13C) : 14.12(q) ; 18.44(q) ; 22.72(t) ; 25.06(t) ; 25.95(t) ; 28.68(t) ; 28.92(t); 29.05(t); 29.21 (t) ; 29.30(t) ; 29.39(t) ; 29.51 (t) ; 29.64(t) ; 29.71(t) ; 31.95(t) ; 33.80(t) ; 34.45(t) ; 58.45(t) ; 64.41 (t) ; 114.17(t) ; 139.16(d) ; 174.07(s) 5 ppm. MS : 394(0, M+), 96(72), 83(70), 82(88), 55(100). q. 1-methylpentyl hexadecanoate NMR(1H 360MHz) : 4.90(m, 1H) ; 2.26(t, 2H) ; 1.65(m, 4H) ; 1.25-1.32(m, 28H) ; 1.20(d, 3H); 0.89(q, 6H) 5 ppm. NMR(13C) : 13.97(q) ; 14.00(q) ; 20.40(q) ; 22.56(t) ; 22.7(t) ; 25.1 (t) ; 27.6(t) ; 29.2(t) ; 29.3(t) ; 29.4(t); 29.5(t) ; 29.6(t) ; 29.7(t) ; 29.73(t) ; 31.97(t); 34.83(t) ; 35.75(t) ; 70.74(d); 173.50(s) 5 ppm. MS : 84(100), 69(50), 57(70), 55(62), 43(98). r. 7-p-menthanyl hexadecanoate NMR(lH, 360MHz) : 0.80-0.95(m, 9H) ; 1.2-2.0(broad m, 37H) ; 2.32(t, 2H) ; 3.88 et 4.02(d, 2H) 5 ppm. NMR(13C) : 14.09(t) ; 19.8(t) ; 20.2(t) ; 22.7(t) ; 25.12(t) ; 22.56(t) ; 26.44(t); 29,10(t); 29.22(t); 29.30(t) ; 29.38(t) ; 29.51 (t) ; 29.63(t) ; 29.71 (t) ; 29.92(t) ; 30.54(d) ; 31.97(t) ; 32.90(d) ; 33.90(d) ; 34.50(t) ; 37.50(d) ; 42.98(d) ; 44.11(d) ; 66.62(t) ; 69.50(t) ; 174.05(s) 5 ppm. MS : 93(70), 77(33), 69(100), 43(48), 41(92). s. hexyl hexadecanoate NMR(lH, 360MHz): 4.02(t, 2H) ; 3.86(broad q, 2H) ; 2.29(t, 2H) ; 1.60(broad m, 4H) ; 1.2-1.4(broad m, 28H) ; 0.90(m, 6H) 5 ppm. NMRC13C) : 14.1(q) ; 13.97(q) ; 22.58(t) ; 22.74(t) ; 25.11(t) ; 25.68(0 ; 28.75(0 ; 29.24(0; 29.34(0; 29.41(0; 29.54(0; 29.67(0; 29.72(0; 29.74(0; 31.51(0 ; 32.00(0 ; 34.50(0 ; 58.42(0 ; 64.46(0 ; 174.07(s) 5 ppm. MS : 340(2, M+), 84(100), 57{55), 56(5S), 43(80). t. (Z)-3-hexenyl hexadecanoate NMR(1H, 360MHz) : 5.45(m, 1H) ; 5.26(m, 1H) ; 4(t, 2H) ; 3.42(s, 4H) ; 2.2- 3.3(111, 8H) ; 2.0(m, 1H) ; 1.6(m, 8H) ; 1.2(broad m, 30H) ; 0.8-1.0(m, 6H) 5 ppm. NMR(13C): 14.14(q); 14.24(q); 20.63(t) ; 22.73(t) ; 25.02(t) ; 25.59(0; 26.37(t); 26.72(0; 26.82(0; 29.20(0; 29.32(0; 29.40(0; 29.51(0; 29.73(0 ; 31.97(0 ; 34.39(0 ; 93.77(0 ; 123.83(d) ; 134.50(d) ; 173.93(s) 5 ppm. MS : 83(25), 82(100), 67(38), 55(27), 43(14). u- (E)-3,7-dimethyl-2,6 octadienyl hexadecanoate NMR(1H, 360MHz) : 0.87(t, 3H) ; 1.26(m, 26H) ; 1.6(s, 3H) ; 1.68(s, 3H) ; 1.70(s, 3H) ; 2.0-2.15(m, 4H) ; 2.30(t, 2H) ; 4.6(d, 2H) ; 5.09(t, 1H) ; 5.35(t, 1H) 8 ppm. NMR(13C) : 14.12(q); 16.48(q) ; 17.69(q) ; 27.73(0; 25.08(0; 25.68(0; 26.38(0 ; 29.22(0 ; 29.33(0 ; 29.41(0 ; 29.53(0 ; 29.67(0 ; 29.72(0 ; 31.99(0 ; 34.45(0 ; 35.59(0 ; 61.19(0 ; 116.60(d) ; 123.85(d) ; 131.80(s); 142.06(s); 173.91 (s) 8 ppm. MS : 392(0, M+), 93(94), 69(100), 43(89), 41(70). Example 2 Preparation de di-esters General method The same method as that described in Example 1 was used, but employing half the molar amounts of the coIResponding diacyl dichloride [(CH2)n[C(0)Cl]2, n=0 to 6]. The following di-esters were prepared according to this general method : a. bis(9-decenyl) oxalate B. p. (bulb-to-bulb distillation): 200°/40 Pa m(CHCl3) : 2930, 2860, 1770, 1740,1460, 1312,1175, 912 cm-1 NMR(1H, 360MHz) : 1.25-1.45(20H) ; 1.74(m, 4H) ; 2.04(broad q, J=7Hz, 4H) ; 4.28(t, J=7Hz, 4H) ; 4.93(broad d, J=llHz, 2H) ; 4.99(broad d, J=17Hz, 2H) ; 5.80(m, 2H) 8 ppm. NMR(13C) : 158.1(s) ; 139.0(d) ; 114.2(t) ; 67.1(t) ; 33.8(0 ; 29.3(0 ; 29.1(t) ; 29.0(t); 28.9(t); 28.3(0 ; 25.7(0 5 ppm. MS : 366(0, M+), 138(9), 109(13), 96(27), 83(55), 69(45), 55(100). bis(9-decenyl) malonate B. p. (bulb-to-bulb distillation): 210°/40 Pa IR(CHC13) : 2940, 2862,1740,1465, 1336,1276,1155, 915 cm-1 NMR(1H, 360MHz) : 1.25-1.45(20H) ; 1.64(m, 4H); 2.04(broad q, J=7Hz, 4H); 3.37(s, 2H) ; 4.14(t, J=7Hz, 4H); 4.93(broad d, J=llHz, 2H) ; 4.99 (broad d, J=17Hz, 2H) ; 5.81(m, 2H) 5 ppm. NMR(13C) : 166.6(s) ; 139.1(d) ; 114.2(t) ; 65.6(0 ; 41.7(0 ; 33.8(0 ; 29.4(0 ; 29.2(t) ; 29.1(0 ; 28.9(0 ; 28.5(0 ; 25.8(0 5 ppm. MS : 380(0, M+), 138(25), 109(21), 105(42), 96(60), 83(100), 68(65), 55(95). bis(9-decenyl) butanedioate IR(CHC13) : 2935, 2860,1735, 1460,1160, 995, 910 crIR-1 NMR(1H, 360MHz) : 1.25-1.45(20H); 1.63(m, 4H) ; 2.04(broad q, J=7Hz, 4H) ; 2.62(s, 4H) ; 4.08(t, J=7Hz, 4H) ; 4.93(broad d, J=llHz, 2H) ; 4.99(broad d, J=17Hz, 2H) ; 5.81 (m, 2H) 8 ppm. NTMR(13C) : 172.3(s) ; 139.1(d) ; 114.2(t) ; 64.9(0 ; 33.8(0 ; 29.4(0 ; 29.3(0 ; 29.2(t) ; 29.1(0 ; 28.9(0 ; 28.7(t) ; 25.9(0 5 ppm. MS : 394(0, M+), 138(10), 119(22). 101(60), 97(38), 83(100), 69(44), 55(76). bis(9-decenyl) pentanedioate IR(CHC13) : 2940, 2880,1740,1464,1180,1000, 918 cm-1 NMR0H, 360MHz) : 1.25-1.45(20H) ; 1.62(m, 4H) ; 1.95(t, J=7, 7Hz, 2H) ; 2.04(broad q, J=7Hz, 4H) ; 2.37(t, J=7Hz, 4H); 4.06(t, J=7Hz, 4H); 4.93(broad d, J=llHz, 2H) ; 4.99(broad d, J=17Hz, 2H) ; 5.81 (m, 2H) 5 ppm. NMR(13C) : 173.0(s) ; 139.1(d) ; 114.2(0 ; 64.6(0 ; 33.8(0 ; 33.4(0 ; 29.4(0 ; 29.2(0 ; 29.1(0 ; 28.9(0 ; 28.7(t); 25.9(0 5 ppm. MS : 408(0, M+), 115(100), 97(14), 87(20), 83(26), 69(19), 55(39). bis(9-decenyl) hexanedioate m(CHCl3) : 2942, 2864,1740,1466,1180,1000, 918 cm-1 NMR(1H, 360MHz) : 1.25-1.45(20H) ; 1.55-1.75(8H) ; 2.04(broad q, J=7Hz, 4H) ; 2.32(m, 4H) ; 4.06(t, J=7Hz, 4H) ; 4.93(broad d, J=llHz/ 2H) ; 4.99(broad d, J=17Hz, 2H) ; 5.81(m, 2H) 5 ppm. NMR(13C) : 173.4(s) ; 139.1(d) ; 114.2(t) ; 64.5(t); 34.0(t) ; 33.8(t) ; 29.4(t) ; 29.2(t); 29.0(t); 28.9(t) ; 28.7(t); 25.9(t); 24.5(t) 5 ppm. MS : 422(0, M+), 129(90), 111(64), 101(31), 95(23), 83(60), 67(41), 55(100). £ (E,E)-bis(3,7-dimethyl-2,6-octadienyl) oxalate IR(CHC13) : 2929, 1740, 1449, 1378, 1302, 1168 cm-1 NMR(lH, 360MHz) : 1.60(s, 6H) ; 1.68(s, 6H) ; 1.75(s, 6H) ; 2.09(8H) ; 4.80(d, J=7Hz, 4H) ; 5.07(m, 2H) ; 5.41 (broad t, J=7Hz, 2H) 5 ppm. NMR(13C) : 158.0(s) ; 144.3(s) ; 132.0(s) ; 123.6(d) 116.9(d) ; 63.8(t) ; 39.6(t) ; 26.2(t) ; 25.7(q) ; 17.7(q) ; 16.6(q) 5 ppm. MS : 362(0, M+), 135(7), 93(20), 81(29), 69(100). g. (E,E)-bis(3,7-dimethyl-2,6-octadienyl) malonate IR(CHC13) : 2930,1728,1447,1379,1278,1149, 983 cm-1 NMR(1H, 360MHz) : 1.60(s, 6M) ; 1.69(s, 6H) ; 1.71(s, 6H); 2.08(8H) ; 3.38(s, 2H) ; 4.65(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.34(broad t, J=7Hz, 2H) 8 ppm. MMR(13C) : 166.6(s) ; 142.9(s) ; 131.9(s) ; 123.7(d) ; 117.8(d); 62.4(t) ; 41.7(t); 39.6(t) ; 26.4(t) ; 25.7(q) ; 17.7(q) ; 16.5(q) 5 ppm. MS : 376(0, M+), 136(17), 121(15), 93(39), 81(33), 69(100). h. (E,E)-bis(3,7-dimethyl-2,6-octadienyl) butanedioate IR(CHC13) : 2930,1729,1446,1384,1231,1162 cm-1 NMR(lH, 360MHz) : 1.61(s, 6H) ; 1.69(s, 6H) ; 1.70(s, 6H) ; 2.08(8H) ; 2.64(s, 4H) ; 4.62(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.34(broad t, J=7Hz, 2H) 5 ppm. NTMR(13C) : 172.3(s) ; 142.3(s) ; 131.8(s) ; 123.8(d) ; 118.3(d) ; 61.7(t) ; 39.6(t) ; 29.3(t) ; 26.4(t) ; 25.7(q) ; 17.7(q) ; 16.5(q) 5 ppm. MS : 390(0, M+), 136(17), 121(19), 93(62), 81(27), 69(100). i- (E,E)-bis(3,7-dimethyl-2,6-octadienyl) pentanedioate IR(CHCl3) : 2930, 1727, 1450, 1232, 1176 cm-1 NMR(lH, 360MHz) : 1.61(s, 6H) ; 1.68(s, 6H) ; 1.70(s, 611) ; 1.96(m, 2H) ; 2.07(8H) ; 2.37(t, J=7Hz, 4H) ; 4.59(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.33(broad t, J-7Hz, 2H) 5 ppm. NMR(13C) : 172.9(s) ; 142.2(s) ; 131.8(s) ; 123.8(d) ; 118.4(d) ; 61.4(t) ; 39.6(t) ; 33.4(t); 26.3(t) ; 25.7(q); 20.3(t); 17.7(q); 16.5(q) 5 ppm. MS : 404(0, M+), 136(20), 121(18), 93(55), 81(48), 69(100). j. (E,E)-bis(3,7-dimethyl-2.6-octadienyl) hexanedioate IR(CHC13) : 2931, 1727, 1446, 1384, 1233, 1174 cm-1 NMROH, 360MHZ): 1.60(S, 6H); 1.68(4H) ; 1.68(s, 6H) ; 1.70(6H) ; 2.07(8H) ; 2.33(4H) ; 4.59(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.33(broad t, J=7Hz, 2H) 5 ppm. NTMR(13C) : 173.3(s) ; 142.2(s); 131.8(s) ; 123.8(d) ; 118.4(d) ; 61.3(t) ; 39.8(t) ; 34.0(t) ; 2.6Ait) ; 25.7(q) ; 24.5(t) ; 17.7(q) ; 16.5(q) d ppm. MS : 418(0, M+), 135(15), 121(15), 93(52), 81(32), 69(100). Example 3 Preparation of enol-esters General method A 500 ml three-neck flask under argon was charged with 0.162 mole of the appropriate aldehyde of formula (Formula Removed) 2.5 g (26 mmole) of anhydrous potassium acetate, 34.45 g (0.34 mole) of triethylamine and 250 ml of acetic anhydride. After heating for 6 h at 120°, the reaction mixture was cooled to room temperature, poured on ice, extracted three times with petroleum ether 30-50°, washed 6 times with 100 ml of saturated NaHCO3, then with water to neutrality. After drying over Na2SO4, filtering, concentrating under vacuum and distilling on a Vigreux column, there was obtained the enolacetate coIResponding to the starting aldehyde, in the form of a mixture of E and Z isomers. The latter were then separated by preparative gas chromatography. When starting from a ketone of formula (Formula Removed) there was followed a method analogous to that described by T. Taapken et al., J. Chem. Soc. Perkin Trans. I, 1994, 1439, wherein the ketone is dissolved in the acetic anhydride and treated with p-toluenesulfonic acid as catalyst, and the formed acetic acid is eliminated to obtain the coIResponding enolacetate. The enolacetates thus prepared are then converted into the enol-esters of formula (I) proceeding as follow. '"A 500 ml three-neck flask under argon was charged with 0.05 mole of enolacetate and 75 ml of absolute tetrahydrofuran. The mixture was cooled to -60/-700 (dry ice/acetone bath) and a solution of 6.16 g (0.055 mole) of t-BuOK in 60 ml of absolute THF was introduced dropwise (slightly exothermic, the reaction mixture becomes strongly yellow). StiIRing was kept for 1 h at -70° and 0.055 mole of the appropriate acyl chloride, in solution in 25 ml of absolute THF, were added dropwise. After 2 h at -70°, the cooling bath was removed and 60 ml of a saturated solution of NaHCO3 were quickly added (the temperature rises quickly to -10°). The mixture was extracted twice with sulfuric ether, washed once with saturated NaHCO3, once with water satured with salt, dried (Na2SO4) and concentrated under vaccum. The product is then purified by flash-chromatography (column diameter = 9 cm, hexane/ether 98:2) and, after combining the useful layers, concentrated to dry under absolute vaccum. According to this method, there were prepared the following enol-esters : a. 2-(4-tert-butylbenzyl)-l-propenyl acetate Isomer (Z) NMR(1H, 360MHZ, CDC13) : 1.32(s, 9H) ; 1.59(s, 3H) ; 2.16(s, 3H) ; 3.43(s, 2H) ; 6.99(broad s, 1H) ; 7.10(d, J=8, 2H) ; 7.31 (d, J=8, 2H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 17.4(q) ; 20.8(q); 31.4(q) ; 31.4(q) ; 31.4(q) ; 35.3(t) ; 125.3(d) ; 125.3(d) ; 128.3(d) ; 128.3(d) ; 130.5(d) ; 34.4(s) ; 121.2(s) ; 136.0(s) ; 149.0(s) ; 168.3(s) 5 ppm. MS : 246(13, M+); m/e, 204(17), 189(73), 171(7), 159(8), 147(31), 129(33), 119(100), 105(9), 91(40), 77(8), 71(7), 57(60), 43(64). Isomer (E) NMR(lH, 360MHz, CDCI3) : l-32(s, 9H) ; 1.62(s, 3H) ; 2.15(s, 3H) ; 3.24(s, 2H) ; 7.05(broad s, 1H) ; 7.12(d, J=8, 2H) ; 7.31 (d, J=8, 2H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 13.6(q) ; 20.8(q) ; 31.4(q) ; 31.4(q) ; 31-4(q) ; 39.8(t); 125.3(d); 125.3(d); 128.4(d); 128.4(d); 131.2(d); 34.4(s) ; 121.4(s) ; 135.9(s) ; 149.2(s) ; 168.3(s) 5 ppm. MS : 246(12, M+); m/e, 204(41), 189(100), 171(3), 159(7), 147(42), 131(21), 119(57), 105(9), 91(32), 77(6), 71(8), 57(45), 43(58). b. 3,7-dimethyl-l ,6-octadienyl acetate The analytical characteristics of this compound were identical to those published in the literature (see, D.P. Simmons et al., ref. cited). c 3,7-dimethyl-l ,6-octadienyl octanoate Isomer (Z) NMR(1H, 360MHZ, CDCI3) : 0.89(t, J=7, 3H) ; 0.99(d, J=7, 3H) ; 1.30(m, 10H) ; 1.59(s, 3H) ; 1.68(s, 3H) ; 1.94(m, 2H) ; 2.39(t, J=7, 2H) ; 2.68(m, 1H) ; 4.67(dd, Ji=6, J2=10, 1H) ; 5.10(m, 1H); 7.00(d, J=6,1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1(q) ; 17.6(q) ; 20.9(q) ; 25.7(q) ; 22.6(t) ; 24.8(t) ; 25.9(t) ; 28.9(t) ; 29.0(t) ; 31.7(t) ; 34.2(t) ; 37.4(t) ; 29.4(d) ; 120.1(d) ; 124.5(d) ; 133.1(d) ; 131.3(s) ; 171.0(s) 5 ppm. MS : 280(0, M+); m/e, 198(1), 182(2), 154(8), 136(35), 127(100), 121(30), 109(20), 93(12), 82(17), 69(23), 57(96), 41(32). Isomer (E) NMR^'H, 360MHz, CDCI3) : 0.89(t, J=7, 3H) ; 1.02(d, J=7, 3H) ; 1.30(m, 10H) ; 1.59(s, 3H) ; 1.68(s, 3H) ; 1.96(m, 2H) ; 2.15(m, 1H) ; 2.36(t, J=7, 2H) ; 5.07(m, 1H); 5.29(dd, Ji=8, J2=12,1H)_; 7.08(d, J=12,1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1(q) ; 17.7(q) ; 20.9(q) ; 25.7(q) ; 22.6(t) ; 24.7(t) ; 25-7(t) ; 28.9(t) ; 29.1(t) ; 31.6(t) ; 34.1 (t) ; 37.2(t) ; 32.0(d) ; 120.4(d) ; 124.3(d) ; 134.6(d) ; 131.5(s) ; 171.2(s) 5 ppm. MS : 280(0, M+); m/e, 198(1), 185(1), 154(7), 136(32), 127(93), 121(26), 109(19), 93(11), 82(15), 69(23), 57(100), 41(32). d. 2-methyl-l-undecenyl acetate Isomer (Z) NMR(!H, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.27(m, 12H) ; 1.39(m, 2H); 1.63(split s, 3H) ; 2.11(m, 2H) ; 2.13(s, 3H); 6.83(broad s, 1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1(q) ; 17.4(q) ; 20.7(q) ; 22.7(t) ; 27.0(t) ; 29.3- 29.6(t) ; 29.3-29.6(t) ; 29.3-29.6(t) ; 29.3-29.6(0 ; 29.3-29.6(t) ; 31.9(t) ; 120.0(d) ; 122.3(s); 168.3(s) 5 ppm. MS : 226(3, M+); m/e, 184(33), 166(1), 141(2), 124(3), 110(6), 95(14), 82(15), 71(100), 57(13), 43(50). Isomer (E) NMR(1H/ 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.27(m, 12H) ; 1.40(m, 2H) ; 1.66(split s, 3H) ; 1.95(m, 2H); 2.13(s, 3H); 6.88(broad s, 1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 13.6(q) ; 14.1(q) ; 20.8(q) ; 22.7(0 ; 27.6(t) ; 29.2(0 ; 29.3(0 ; 29.5(t) ; 29.6(t) ; 31.9(t); 33.9(t) ; 130.2(d) ; 122.0(s); 168.3(s) 5 ppm. MS : 226(2, M+); m/e, 184(25), 166(1), 141(2), 123(3), 110(5), 95(12), 81(18), 71(100), 58(9), 43(40). e. 2-methyl-l-undecenyl octanoate Isomer (Z) NMR(lH, 360MHz, CDCI3) : 0.88(t, J=7, 6H) ; 1.27(m, 22H) ; 1.39(m, 2H) ; 1.52(split s, 3H) ; 2.10(t, J=7, 2H) ; 2.37(t, J=7, 2H) ; 6.85(broad s, 1H) 8 ppm. NMR(13C, 90MHz, CDCI3) : 14.0(q) ; 14.1(q) ; 17.4(q) ; 22.6(t) ; 22.7(t) ; 24.9(t) ; 27.1(t) ; 28.9-29.6(0 ; 28.9-29.6(t) ; 28.9-29.6(t) ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 31.7(0 ; 31.9(0 ; 34.2(0 ; 129.9(d) ; 122.2(s) ; 171.l(s) 5 ppm. MS : 310(0, M+); m/e, 184(10), 127(85), 109(10), 95{6\ 81(10), 71(25), 57(100), 43(10). Isomer (E) NMR(1H, 360MHz, CDCI3) : 0.88(t, J=7, 6H) ; 1.27(m, 22H) ; 1.40(m, 2H); 1.67(split s, 3H) ; 1.95(t, J=7, 2H) ; 2.39(t, J=7, 2H) ; 6.89(broad s, 1H) 5 ppm. NMR^SC, 90MHz, CDCI3) : 13.6(q) ; 14.0(q) ; 14.1 (q) ; 22.6(0; 22.7(0; 24.9(0 ; 27.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 31-7(0 ; 31.9(0 ; 34.0(t) ; 34.2(0 ; 130.1(d); 121.9(s) ; 171.l(s) 5 ppm. MS : 310(0, M+); m/e, 184(10), 127(87), 109(10), 97(7), 81(13), 71(28), 57(100), 43(9). f. 1-undecenyl acetate Isomer (Z) NTMR(1H, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.28(m, 12H) ; 1.37(m, 2H) ; 2.12(m, 2H); 2.14(s, 3H) ; 4.87(dt, J1=J2=6, 1H) ; 6.99(d, J=6, 1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1 (q) ; 20.8(q) ; 22.7(0 ; 24.4(0 ; 29.2-29.6(0 ; 29.2-29.6(0 ; 29.2-29.6(0 ; 29.2-29.6(0 ; 29.2-29.6(0 ; 31.9(0 ; 114.4(d) ; 134.0(d) ; 168.2(s) 5 ppm. MS : 212(0, M+); m/e, 170(1), 152(3), 124(5), 110(6), 96(26), 82(34), 68(18), 57(33), 43(100). Isomer (E) NMROH, 360MHz, CDC13) : 0.88(t, J=7, 3H) ; 1.27(m, 12H) ; 1.37(m, 2H) ; 1.99(q, J=7, 2H) ; 2.11(s, 3H) ; 5.41(dt, Ji=7, J2=12, 1H) ; 7.06(d, J=12, 1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1 (q) ; 20.7(q) ; 22.7(0 ; 27.3(t) ; 29.1-29.6(0 ; 29.1-29.6(t) ; 29.1-29.6(0 ; 29.1-29.6(0 ; 29.1-29.6(0 ; 31.9(0 ; 115.1(d) ; 135.4(d) ; 168.3(s) 5 ppm. MS : 212(0, M+); m/e, 170(1), 152(4), 124(7), 110(8), 96(34), 82(41), 68(19), 57(39), 43(100). 3-methyl-5-phenyl-l-pentenyl acetate Isomer (Z) NTMR(1H, 360MHz, CDCI3) : 1.02(d, J=7, 3H) ; 1.54(m, 1H) ; 1.69(m, 1H) ; 2.10(s, 3H) ; 2.48-2.78(m, 311) ; 4.72(dd, Ji=6, J2=10, 1H) ; 7.03(d, J=6, 1H) ; 7.17(m, 3H) ; 7.26(m, 2H) 5 ppm. NTMR(13C, 90MHz, CDCI3) : 20.7(q) ; 21.0(q) ; 33.7(0 ; 38.9(0 ; 29.2(d) ; 119.8(d) ; 125.6(d) ; 128.2(d) ; 128.2(d) ; 128.4(d) ; 128.4(d) ; 133.4(d) ; 142.5(s) ; 168.1 (s) 5 ppm. MS : 218(1, M+); m/e, 176(3), 158(39), 143(27), 131(10), 117(6), 104(16), 91(45), 71(43), 65(13), 51(7), 43(100). Isomer (E) NMR(lH, 360MHz, CDCI3) : 1.06(d, J=7, 3H) ; 1.62(m, 2H) ; 2.12(s, 3H); 2.18(m, 1H) ; 2.60(m, 2H) ; 5-33(dd, Ji=9, J2=13, 1H) ; 7.09(d, J=13, 1H) ; 7.17(m, 3H) ; 7.27(m, 2H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 20.7(q) ; 21.0(q) ; 33.5(0 ; 38.8(t) ; 32.1(d) ; 120.3(d) ; 125.7(d) ; 128.3(d) ; 128.3(d); 128.4(d) ; 128.4(d) ; 134.9(d) ; 142.3(s) ; 168.3(s) 5 ppm. MS : 218(1, M+); m/e, 176(4), 158(34), 143(25), 131(9), 117(5), 104(16), 91(44), 71(48), 65(12), 51(6), 43(100). 3-methyl-5-phenyl-l -pentenyl octanoate Isomer (Z) KTMROH, 360MHz, CDCI3) : 0.89(t, J=7, 3H) ; 1.02(d, J=7, 3H) ; 1.30(m, 8H) ; 1.49-1.76(m, 4H) ; 2.36(t, J=7, 2H) ; 2.48-2.78(m, 3H) ; 4.72(dd, Jl=7, J2=10, 1H) ; 7.05(d, J=7, 1H) ; 7.17(m, 3H) ; 7.26(m, 2H) 5 ppm. NTMR03C, 90MHz, CDCI3) : 14.1(q) ; 21.0(q) ; 22.6(t) ; 24.7(t) ; 28.9(t) ; 29.0(t); 31.7(0 ; 33.7(0 ; 34.1(t) ; 38.9(0 ; 29.3(d); 119.7(d) ; 125.6(d); 128.2(d) ; 128.2(d) ; 128.4(d) ; 128.4(d) ; 133.4(d) ; 142.5(s) ; 171.0(s) S ppm. MS : 308(0, M+); m/e, 176(8), 158(78), 143(18), 127(100), 104(36), 91(51), 71(10), 57(71), 43(14). Isomer (E) NMROH, 360MHz, CDCI3) : 0.89(t, J=7, 3H) ; 1.07(d, J=7, 3H) ; 1.30(m, 8H) ; 1.65(m, 4H) ; 2.18(m, 1H) ; 2.37(t, J=7, 2H) ; 2.60(m, 2H) ; 5.33(dd, J1=8, J2=12, 1H) ; 7.10(d, J=12, 1H) ; 7.17(m, 3H) ; 7.27(m, 2H) 8 ppm. NTMR(13C, 90MHz, CDCI3) : 14.1(q) ; 21.0(q) ; 22.6(t) ; 24.7(t) ; 28.9(0 ; 29.0(t) ; 31.6(t) ; 33.6(0 ; 34.1(0 ; 38.9(0 ; 32.1(d) ; 120.1(d); 125.7(d) ; 128.3(d) ; 128.3(d) ; 128.4(d) ; 128.4(d) ; 135.0(d); 142.54(s) ; 171.l(s) 8 ppm. MS : 308(0, M+); m/e, 198(1), 176(10), 158(66), 143(20), 127(95), 104(34), 91(56), 71(13), 57(100), 43(20). i. methyl 3-acetoxy-2-pentyl-2-cvclopentene-1 -acetate NMR('H, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.28(m, 5H) ; 1.41(m, 1H) ; 1.61(m, 1H) ; 1.79(m, 1H) ; 2.14(s, 3H) ; 2.03-2.26(m, 3H) , 2.46(m, 2H) ; 2.56(dd, Ji=4, J2=15, 1H) ; 3.04(m, 1H) ; 3.68(s, 3U) 8 ppm. NMR(13C, 90MHz, CDCI3) : 14.0(q) ; 20.7(q) ; 51.5(q) ; 22.4(0 ; 24.5(0 ; 26.8(0 ; 27.2(0 ; 29.6(0 ; 31.7(t) ; 38.6(0 ; 39.7(d) ; 128.3(s) ; 145.4(s) ; 168.5(s) ; 173.2(s) 5 ppm. MS : 268(1, M+); m/e, 226(10), 208(2), 195(3), 169(3), 153(100), 137(4), 123(3), 109(10), 97(35), 83(10), 67(9), 55(8), 43(31). j. methyl 3-octanoyloxy-2-pentyl-l-cyclopentene-l-acetate NMR(lH, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 0.89(t, J=7, 3H) ; 1.30(m, 14H) ; 1.53-1.72(m, 3H) ; 1.79(m, 1H) ; 2.08(m, 1H) ; 2.19(m, 2H) ; 2.31-2.51 (m, 4H) ; 2.57(dd, ft =4, J2=15, 1H) ; 3.05(m, 1H) ; 3.68(s, 3H) 8 ppm. NMR(13C, 90MHz, CDCI3) : 14.0(q) ; 14.1 (q) ; 51.5(q) ; 22.4(0; 22.6(0; 24.5(0 ; 25.0(0 ; 26.8(0 ; 27.1(0 ; 28.9(0 ; 29.1(0 ; 29.6(0 ; 31.7(0 ; 31.7(0 ; 34.2(t); 38.6(0 ; 39.6(d) ; 128.2(s) ; 145.3(s) ; 171.5(s) ; 173.3(s) 6 ppm. MS : 352(0, M+); m/e, 279(2), 226(92), 208(3), 194(4), 169(4), 153(100), 127(12), 109(7), 97(6), 81(5), 67(5), 57(22), 43(10). Example 4 Test on fabrics Several tests were caIRied out on fabrics, under a variety of conditions, said fabrics having been treated according to the following general method. General method of treatment of textiles A standard cotton swatch of 32 g was placed in a Linitest ® (origin : Manau, Germany) type vessel containing 1.3 g of a standard powder detergent base comprising 1% by weight of lipase (Lipolase ® 100T; origin : Novo Nordisk, Denmark) and 260 ml water. The cotton swatch was washed for 30 min at 40°. It was then taken out of the vessel and rinsed with 3x200 ml of water. It was then plunged for 5 min in 200 ml of water containing 0.6 g of a fabric softener base which contained a certain percentage by weight, comprised between 0.05 and 1%, of compound (I) according to the invention or, when applicable, of the coIResponding alcohol, aldehyde or ketone. The cotton swatch was then spin-dried without having been rinsed, and dried on a clothes line. This method is equivalent to a washing in a real machine for washing 5 kg of linen in approximately 20 1 of water, with a rinsing of 4x20 1 water, the fabric softener being applied in the last rinsing water. The fabric softener base used had the following composition : Ingredients % by weigth Arquad 2 HT D (75%) 5.00 Formalin (40%) 0.20 Demineralized water 94.69 Colouring agent 2) 0.11 Total 100.00 1) origin : Akzo, Holland 2) Colanyl Blau AR/10% sol.; origin : Hoechst, Germany In two separate tests, the cotton swatches were treated according to this general method, using as additive to the fabric softener respectively 9-decenyl hexadecanoate (1% by weight) in test A and 9-decenol (1% by weight) in test B. The two swatches were submitted for a blind test evaluation 24 h after having been taken out of the Linitest ® apparatus. The evaluation panel consisted of eight people, to whom had been given beforehand a smelling strip which had been dipped in 9-decen-l-ol, so as to render them familiar with the odour of this compound. The panel was then asked to smell the two cotton swatches above-mentioned and to indicate if they could identify the odour of 9-decen-l-ol in either of the swatches. Five amongst the eight members of the panel recognized the odour of this alcohol in the swatch treated in test A and indicated that this odour was very powerful, whereas only one of said members was able to identify the odour on the swatch treated in test B. A further evaluation of the two swatches caIRied" out by the same panel, under identical conditions, 24 h later, i.e. 48 h after taking the swatches out of the Linitest ® apparatus, showed that none of the panel members could identify the odour of 9-decen-l-ol on the swatch of test B, whereas six of said members identified it without any hesitation on the swatch coming out of test A. Similar results were obtained when the two compounds above-mentioned were present in the fabric softener at a rate of 0.5% by weight. Example 5 Test on fabrics Nine standard cotton swatches (32 g each), numbered from 1 to 9, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener (at 1 % by weight) and described in Table 1 hereinafter. TABLE 1 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the nine cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having smelled 9-decen-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 2 hereafter (only categorical identifications were taken into account) : TABLE 2 (Table Removed) In a similar test caIRied out 48 h after having taken the swatches out of the Linitest ® machine, the members of the panel were still unanimous as regards swatch 1, i.e. they could not recognize the odour of 9-decen-l-ol on this swatch, whereas a majority judged it still very powerful on all the other swatches. Example 6 Test on fabrics Six standard cotton swatches (32 g each), numbered from 1 to 6, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener (at 1 % by weight) and described in Table 3 hereinafter. TABLE 3 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the six cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having smelled 9-decen-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 4 hereafter (only categorical identifications were taken into account) : TABLE 4 (Table Removed) The same test, caIRied out 48 h after having taken the swatches out of the Linitest ® machines, gave the results summarized in Table 5 hereinafter : TABLE 5 (Table Removed) Example 7 Test on fabrics Six standard cotton swatches (32 g each), numbered from 1 to 6, were separately treated, and in identical manner, as described in Example 4. The detergent's content in lipase was now 3% by weight and the amount of fabric softener added to the last rinsing water was now 1.2 g. The additive incorporated (at 1% by weight) into the fabric softener in each case is cited in the following Table 6 : TABLE 6 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the six cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having smelled (E)-3,7-dimethyl-2,6-octadien-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 7 hereafter (only categorical identifications were taken into account) : TABLE 7 (Table Removed) Example 8 Test on fabrics Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener and described in Table 8 hereinafter. TABLE 8 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of eleven individuals, whom, after having smelled (E)-3,7-dimethyl-6-octen-1-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on one or the other of the swatches- The result of this evaluation is summarized on Table 9 hereafter (only categorical identifications were taken into account) : TABLE 9 (Table Removed) A similar test caIRied out with two cotton swatches treated with the same fabric softener base but containing only 0.5% by weight of the compounds reported in Table 8. The panel evaluation showed that none of the panel members was able to identify the odour of the alcohol on swatch 1, whereas 7 of the 11 members of the panel were certain that they could smell it on swatch 2. Still analogous results were obtained with a dosage of 0.1% by weight of the above-mentioned compounds. Example 9 Test on fabrics Three standard cotton swatches (32 g each), numbered from 1 to 3, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener (at 1% by weight) and described in Table 10 hereinafter. TABLE 10 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the three cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having srnelled 3-methyl-5-phenylpentan-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 11 hereafter (only categorical identifications were taken into account) : TABLE 11 (Table Removed) Example 10 Test on fabrics Three standard cotton swatches (32 g each) were treated separately following the general method described in Example 4, two of said swatches (1 et 2) using 9-decen-l-ol as additive to the softener, and swatch 3 using as additive 9-decenyl hexadecanoate, these additives having been added to the fabric softener in a concentration of 0.5% by weight. The three swatches were evaluated on a blind test by a panel of 12 individuals 24 h after having been taken out of the Linitest ® machines. The members of the panel were asked if they could ascertain any difference amongst the swatches and, if applicable, whether they could qualify this difference. The panel had previously smelled strips dipped in 9-decen-l-ol and was aware that an evaluation of the three cotton swatches with regard to the particular odour of this compound was expected. As a result of this evaluation, 8 out of the 12 members of the panel chose swatch 3 as being the one olfactively distinct and indicated that it developed the characteristic odour of 9-decen-l-ol, whilst the other two swatches gave off no distinctive odour. The same test was caIRied out with 1% of additive in the softener, instead of 0.5%. In this case, 9 of the 12 members of the panel chose once again swatch 3 as being the one developing the odour of the above-mentioned alcohol, and indicated that this odour was even more powerful than in the preceding test. On the other hand, the panel found that the other two cotton swatches still exhaled no distinctive odour. Example 11 Test on fabrics Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener, at a rate of 0.05% by weight, and described in Table 12 hereinafter. TABLE 12 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of twelve individuals, whom, after having smelled 3,7-dimethyl-2,6-octadien-1-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on one or the other of the swatches. The result of this evaluation is summarized on Table 13 hereafter (only categorical identifications were taken into account) : TABLE 13 (Table Removed) Example 12 Test on fabrics Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, but adding to the fabric softener 1% by weight of the additives cited in Table 14 hereinafter. TABLE 14 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of eleven individuals, whom, after having smelled 3,7-dimethyl-6-octenal on a smelling strip, had to indicate whether they recognized the odour of this aldehyde on one or the other of the swatches. The result of this evaluation is summarized on Table 15 hereafter (only categorical identifications were taken into account) : TABLE 15 (Table Removed) Example 13 Test on fabrics Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated (at 1% by weight) in the fabric softener and described in Table 16 hereinafter. TABLE 16 (Table Removed) 24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of twelve individuals, whom, after having smelled 3-methyl-5-phenyl-l-pentanal on a smelling strip, had to indicate whether they recognized the odour of this aldehyde on one or the other of the swatches. The result of this evaluation is summarized on Table 17 hereafter (only categorical identifications were taken into account) : TABLE 17 (Table Removed) Example 14 Test on fabrics Three standard cotton swatches (32 g each) were treated separately following the general method described in Example 4, two of said swatches (1 et 2) using 2-methyl-l-undecanal as additive to the softener, and swatch 3 using as additive 2-methyl-l-undecenyl octanoate, these additives having been added to the fabric softener in a concentration of 0.1% by weight. The three swatches were evaluated on a blind test by a panel of 12 individuals 24 h after having been taken out of the Linitest ® machines. The members of the panel were asked if they could ascertain any difference amongst the swatches and, if applicable, whether they could qualify this difference. The panel had previously smelled strips dipped in 2-methyl-l-undecanal and was aware that an evaluation of the three cotton swatches with regard to the particular odour of this compound was expected. As a result of this evaluation, 10 out of the 12 members of the panel chose swatch 3 as being the one olfactively distinct and indicated that it developed the characteristic odour of 2-methyl-l-undecanal, whereas the other two swatches gave off no distinctive odour. Example 15 Test on fabrics treated in a washing machine r Two standard batches of cotton textiles, each comprising 30 cotton swatches (32 g each), were put into two separate washing machines, each containing, in the detergent compartment, 130 g of a standard powder detergent base comprising 1% by weight of lipase (Lipolase ® 100T; origin : Novo Nbrdisk, Denmark). In the compartment intended for the fabric softener, there was put, in one of the cases, 100 g of a softener base such as described in Example 4, perfumed with-0.1% by weight of 2-methyl-l-undecanal, whereas the softener (100 g) put in the second machine contained 0.1% by weight of 2-methyl-1-undecenyl octanoate. The batches of swatches were then washed with a normal washing cycle, at 40°, without prewash, and air dried. The batches of swatches were evaluated on a blind test, 24 h after having been taken out of the machines, by a panel of 36 individuals. The latter had to indicate if they found any difference at all amongst the three batches of swatches, of which two were identical and had been treated with the softener containing 2-methyl-l-undecanal (batches 1 and 2) and the third had been treated with 2-methyl-l-undecenyl octanoate (batch 3), without qualifying the nature of the distinctive character. In addition, they were also asked to indicate whether any one of the batches possessed a more powerful odour. Of the 36 panellists, 24 identified textile batch 3 as being the one distinct from the other two, from an olfactive point of view, and indicated that this batch possessed a stronger odour than the other two. An analogous test was caIRied out but with only two textile batches, batch A having been treated with a softener containing 0.05% by weight of 2- methyl-1-undecanal and batch B with a softener containing 0.05% by weight of the coIResponding enol-ester, i.e. 2-methyl-l-undecenyl octanoate. The panel of 36 individuals which evaluated batches A and B, without knowing the nature of the perfuming ingredients, had to indicate which of the two batches developed a stronger odour and which was prefeIRed from the point of view of the perception of freshness and cleanliness of the linen. According to the categoric opinion of 32 out of the 36 panellists, the textiles batch B was far more "perfumed" than batch A and was perceived as being cleaner, with a more fresh odour. Example 16 Tests on fabrics treated in a washing machine A base perfuming composition was prepared by admixing the following ingredients : (Table Removed) 1) trimethyI-13-oxabicyclo[10.1.0]trideca-4,8-diene; origin: Firmenich SA, Geneva, Switzerland 2) dodecahydro-3,6,6,9a-tetramethyl-naphto[2,l-b]furan ; origin : Firmenich SA, Geneva, Switzerland 3) tricyclo[5.2.1.02,6]dec~3-en-8-yl acetate; origin: Givaudan-Roure, Vernier, Switzerland 4) 2,6-dimethyl-7-octen-2-ol; origin : International Flavors & Fragrances, USA 5) l-(5,5-dimethyl-l-cyclohex-l-yl)-4-penten-l-one ; origin : Firmenich SA, Geneva, Switzerland 6) oxacyclohexadecan-2-one; origin : Firmenich SA, Geneva, Switzerland 7) origine : Firmenich SA, Geneva, Switzerland 8) methylionone; origin : Firmenich SA, Geneva, Switzerland 9) 3-(4-tert-butyl-l-phenyl)-2-methylpropanal; origin : Givaudan-Roure, Vernier, Switzerland 10) 4-(l,l-dimethylethyl)-cyclohexanol acetate ; origin : Firmenich SA, Geneva, Switzerland 11) cis-4-(l-methylethyl)-cyclohexanemethanol ; origin : Firmenich SA, Geneva, Switzerland 12) methyl ester of 3-oxo-l-pentyl~cyclopentaneacetic acid ; origin : Firmenich SA, Geneva, Switzerland 13) origin : Firmenich SA, Geneva, Switzerland 14) 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4~penten-2-ol; origin : Firmenich SA, Geneva, Switzerland 15) octahydro-5-methoxy-4,7-methano-lH-indene-2-carboxaldehyde; origin ; Firmenich SA, Geneva, Switzerland 16) 2,2,5-trimethyl-5-pentyl-cyclopentanone ; origin : Firmenich SA, Geneva, Switzerland 17) 2-tert-butyl-cyclohexanyl acetate; origin : International Flavors & Fragrances, USA 18) 2,4-dimethyl-3-cyclohexene-l-carbaldehyde ; origin : Firmenich SA, Geneva, Switzerland Two perfuming compositions were prepared with this base composition, by adding thereto 150 parts by weight of geraniol or 3,7-dimethyl-2,6-octadienol (composition A), respectively 150 parts by weight of 3,7-dimethyl-2,6-octadienyl hexadecanoate (composition B). These two perfuming compositions were then added, at the rate of 0.6% by weight, to a non-perfumed fabric softener base to prepare two samples, A and respectively B, of a perfumed softener. In two identical washing machines, there were treated two standard batches of textiles, each formed of 1400 g of varied linen, comprising cotton swatches, cotton textiles and textiles in a cotton/polyester mixture. Each machine was charged with 130 g of a standard unperfumed detergent base containing 1% of lipase (Lipolase ® 100T). One of the machines was also charged with 100 g of sample A of the softener, comprising geraniol, whereas to the second machine there were added 100 g of softener sample B. The linen was then washed at 40° in a normal washing cycle, without prewash, and dried to air for 24 h. Three standard batches of textiles, of which two were identical and had been treated with sample A and the third with sample B, were then evaluated on a blind test by a panel of 20 individuals, who had to identify the batch of textiles possessing a distinct odour from that of the other two, without qualifying the nature of the distinctive character. The panellists also had to indicate which of the textile batches was more perfumed. As a result of this test,, 14 panellists perceived a distinction in the odour of the textile batch treated with the fabric softener sample B, while 10 out of these 14 indicated that this same batch was the more perfumed. When the evaluation was repeated after 48 h of drying to air, analogous results were obtained. We claim: 1. An ester of formula (I), as precursor of fragrant alcohol or ketone or aldehyde (Formula Removed) wherein a. R represents a radical derived from an fragrant alcohol of formula ROH and Y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical, or a -(CH2)nCOOR group wherein R is defined as above and n is an integer from 0 to 6; or b. Y represents a C7 to C24 linear or branched, saturated or unsaturated, alkyl radical and R represents a group of formula (Formula Removed) wherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formula (Formula Removed) or R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from an fragrant ketone of formula (Formula Removed) and, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted. 2. A compound as claimed in claim 1, wherein R is the 9-decen-l-yl, 3,7-dimethyl-2,6-octadien- 1-yl, 3,7-dimethyl-6-octen-l -yl, 3-methyl-5-phenylpentyl, 3,7- dimethyl- 1,6-octadienyl, 3-methyl-5-phenyl-l-pentenyl or 2-methyl-l-undecenyl radical. 3. A compound as claimed in claim 1 or 2, wherein Y is a C12 to C24 linear alkyl radical.

Full Text

The present application is divisional of Indian Patent Application No. 191/DEL/1995.
The present invention relates to an ester of formula (I) as precursor of fragrant alcohal or ketone or aldehyde.
The present invention- relates to the field of perfumery and, mon particularly, to improved perfumed detergents and fabric softeners.
The use of enzymes in fabric detergents, in order to improve theii efficiency/ has been known for a number of years. Amongst said enzymes, lipases are particularly preferred, as a result of their capacity to hydrolyse the fat materials on the dirty linen and thus to facilitate its cleaning. However, it is known that xnalodour problems can occasionally occur under certain application conditions. In order to solve these malodour problems, there has been proposed a method (see for example EP 430 315) consisting in carefully choosing the perfuming ingredients incorporated in the detergents and which, following the washing, are deposited on the fabrics. Therefore, appropriate perfuming of said detergents appears to be extremely important.
On the other hand, it would be desirable that said detergents and fabric softeners are able to impart to the fabrics a long-lasting odour, such that the user perceives this odour even a long time after the textiles have been washed and subsequently dried. To this end, it has been known, to use in the fabric detergents and softeners perfuming ingredients which have a good tenacity on the fabrics, i.e. ingredients whose odour, once imparted to the textiles upon the washing, can then be perceived hy the consumer for several days. However, there are many perfuining substances .known for their extremely pleasant odours, and namely a quality of "freshness" often associated with the notion of cleanliness, which substances are unfortunately not very tenacious, or even not tenacious at all, on fabrics, such that their perfuming effect can only be perceived very briefly, at the most for a few hours following the washing and drying operations. Clearly, prolonging the fragrance effect of such substances, and thus the "freshness" of the fabrics, would be highly desirable.
The present invention brings precisely a novel solution to this problem. We have now unexpectedly discovered a better process for perfuining textiles washed -with detergents containing lipases. We have in fact been able to establish that, by adding particular ingredients to the fabric detergent and/or to the fabric softener that is subsequently applied, one could distinctly improve the odour of the fabrics treated with theseproducts and prolong in a remarkable way the fragrance of said fabrics after drying.
A first object of the present invention is thus to provide a process for perfuming fabrics washed in the presence of a Kpase-containing detergent and, optionally, subsequently treated with a fabric softener, said process being characterized in that said detergent and/or said fabric softener contains a compound of formula
(Formula Removed)
wherein
a. R represents a radical derived from a fragrant alcohol of formula ROH
and Y represents a C7 to C24 linear or branched, saturated or
unsaturated alkyl radical, or a -(CH2)nCOOR group wherein R is
defined as above and n is an integer from 0 to 6 ; or
b. Y represents a C7 to C24 linear or branched, saturated or unsaturated
alkyl radical and R represents a group of formula
wherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formula
(Formula Removed)
or R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from a fragrant ketone of formula
and, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted.
By an alkylidene radical derived from a fragrant aldehyde or ketone, it is understood here a radical which, upon the conversion of enol-ester (I) into said aldehyde or ketone, regenerates the corresponding R group which is the substituent of said aldehyde or ketone. Thus, for example, when the fragrant aldehyde is 3,7-dimethyl-6-octenal (R is 3,7-dimethyl~6-octenyl), the corresponding alkylidene radical in enol-ester (I) is 3,7-dimethyl-l,6-octadienyl.
According to a variant of the invention, there is provided a process for perfuming fabrics washed in the presence of a lipase-containing detergent, which process comprises the treatment of said fabrics, after the washing cycle, with a fabric softener containing a compound of formula (I) as defined above.
By "fragrant alcohol", "fragrant aldehyde" or "fragrant ketone" it is meant here any alcohol, aldehyde, respectively ketone, of current use in perfumery, which is capable of imgajrjting an odour to fabrics or textiles,^ upon the process of washing and/or the treatment with a fabric softener. We have in fact discovered that the perfuming effect of such compounds could be remarkably improved, and namely their diffusion prolonged, if they were replaced by the corresponding compound (I) in the detergent or fabrt softener used.
This result is all the more surprising in that the compounds (I) are themselves either devoid of odour, or they possess weak and characterless odours, and are thus apparently useless for perfumery. Yet, when used according to the invention, they are not only capable of imparting to the fabrics the characteristic odour of the corresponding alcohol, aldehyde or ketone, but also of prolonging their effect of diffusion, such that said odour develops itself for much longer periods of time than in the case where said corresponding alcohol, aldehyde or ketone is directly added to the detergents or fabric softeners. Therefore, the use of compounds (I) according to the process of the invention is translated into an enhanced"*1 substantivity of the corresponding alcohols, aldehydes and ketones.
The advantages of this process are all the more obvious in the case of the numerous odoriferous alcohols which are known to be weakly tenacious on washed fabrics and the odour of which, although distinctly perceived when the fabrics are removed from the washing machine, does not remain on the linen and can no longer be perceived after 12 to 24 h.
Many examples of such alcohols can be found in the prior art, some of which only contribute to the odour of the fabrics for a very short
time, and no doubt many others will be discovered in the future. For all these alcohols, the process according to the invention makes it possible to remarkably improve their odoriferous performance on fabrics, by prolonging the diffusion time of their characteristic notes and thus the time during which they contribute significantly to the overall odour. We have in fact established that the use of the corresponding compounds (I) in the detergents and/or fabric softeners made it possible to obtain a perfuming effect equivalent to the one that would have been observed with the prolonged diffusion ("slow-release") of the alcohol, if such a diffusion would have been possible, which is not the case in practice.
Quite clearly, it is impossible to list in an exhaustive manner all the alcohols of formula ROH known to this day, which are capable of imparting pleasant odours to the textiles treated with the laundry products perfumed by way of said alcohols, and the perfuming effect of which can be remarkably improved according to the invention. However, by way of example, one can cite alcohols such as anisic alcohol, cinnamic alcohol, fenchylic alcohol, 9-decen-l-ol, phenethylol, citronellol, 3-methyl-5-phenyl-1-pentanol (origin : Firmenich SA, Geneva, Switzerland), Mayol ® (7-p-menthan-1-ol ; origin : Firmenich SA, Geneva, Switzerland), dihydromyrcenol (2,6-dimethyl-7~octen-2-ol), geraniol (3,7-dimethyl-2,6~ octadien-1-ol), (Z)-3-hexen-l-ol, 1-hexanol, 2-hexanol, 5-ethyl-2-nonanol, 2,6-nonadien-l-ol, borneol, l-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol (origin : Firmenich SA, Geneva, Switzerland), 2-methyl-4-phenyl-2-butanol, 2-methyl-l-phenyl-2-propanol, cyclomethylcitronellol, decanol, dihydroeugenol, 8-p-menthanol, 3,7-dimethyl-l-octanol, 2,6-dimethyl-2-heptanol, dodecanol, eucalyptol, eugenol, Florol ® (tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol; origin : Firmenich SA, Geneva, Switzerland), isoeugenol, linalol, Tarragol ® (2-methoxy-4-propyl-l-cylohexanol; origin : Firmenich SA, Geneva, Switzerland), terpineol, tetrahydromuguol, 3,7-dimethyl-3-octanol and Lyral ® (3 and 4-(4-hydroxy-4-methylpentyl)~ cyclohex-3-ene-l-carbaldehyde ; origin : International Flavors and Fragrances, USA).
It is quite obvious, however, that the process of the invention is perfectly general and can relate to many other alcohols which the skilled person is quite able to choose from the general knowledge in the art and as a function of the olfactive effect it desires to achieve.
Analogous considerations apply to the aldehydes of formula
(Formula Removed)
and to the ketones of formula
(Formula Removed)
The process of the invention is advantageous whenever the compounds such as those mentioned above show a weak tenacity on fabrics, and there are many odoriferous aldehydes and ketones whose performance on textiles turns out to be disctinctly improved when these compounds exert their perfuming activity by way of the corresponding enol-esters of formula (I).
Again, although one cannot cite in an exhaustive manner all the fragrant aldehydes and ketones which can be used according to the process of the invention, there can be cited, by way of example, compounds such as C6 to C12 aldehydes, hydratropic aldehyde, methyl nonyl acetaldehyde, phenylpropanoic aldehyde, Acropal ® [3- or 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde ; origin : Givaudan-Roure, Vernier, Switzerland], 2-methyldecanal, 4-isopropyl-l-benzeneacetaldehyde, (4-methyl-l-phenyl)acetaldehyde, Z-6-nonenal, citral, citronellal, 9-decenal, 3-(4-isopropyl-l-phenyl)-2-methylpropanal (origin : Firmenich SA, Geneva, Switzerland), (E,E)-2,4-heptadienal, (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal, 5,9-dimethyl-4,9-decadienaI, (Z)-6-octenal, Farenal ® (2,6,10-trimethyl-9-undecenal; origin : Givaudan-Roure, Vernier, Switzerland), Foliaver ® [3-(4-methoxy-l~phenyl)-2-methylpropanal ; origin : International Flavors and Fragrances, USA], Heliopropanal ® [3-(l,3-benzodioxol-5-yl)-2-methylpropanal; origin : International Flavors and Fragrances, USA], (Z)-4-heptenal, le 3,5,5-trimerhylhexanal (origin : International Flavors and Fragrances, USA), (4-methyl-l-phenoxy)acetaldehyde, hydroxycitronellal, isocyclocitral (origin : International Flavors and Fragrances, USA), Lilial ® [3-(4-tert-butyl-l-phenyl)-2-methylpropanal ; origin : Givaudan-Roure, Vernier, Switzerland], le l-p-menthene-9-carbaldehyde (origin : Firmenich SA, Geneva, Switzerland), Lyral ® [3- and 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde ; origin : International Flavors and Fragrances, USA], 2,6-dimethyl-5-heptenal, l-p-menthen-9-al, (E)-2-octenal, (2E,6Z)-2,6-
nonadienal, 3-methyl-5-phenylpentanal, (E)-4-decenal, (E)-2-undecenal, 3,7-dimethyloctanal, Zestover (2,4-dimethyl-3-cyclohexene-l-carbaldehyde; origin : Firmenich SA, Geneva, Switzerland), 3-phenylbutanal, Scentenal ® (octahydro-5-methoxy-4,7-methano-lH-indene-2-carboxaldehyde ; origin : Firmenich SA, Geneva, Switzerland), 2,5,9-trimethyl-4,9-decadienal, Intreleven aldehyde (undecenal ; origin : International Flavors and Fragrances, USA), 4-methyl-phenyl-propanoic aldehyde, 4-(4-hydroxy-l-phenyl)-2-butanone, benzylacetone, the ionones, 3-(4-tert-butyl-l-phenyl)propanal, carvone, 3,7-dimethyl-l,l-bis(ll-methyldodecyloxy)-2,6-octadiene, muscone, 2-pentyl-l-cyclopentanone, l'ethyl amyl ketone, l'ethyl pentyl ketone, la 2-heptyl-l-cyclopentanone, geranylacetone, Iralia ® (methylionone ; origin : Firmenich SA, Geneva, Switzerland), Iso E super [l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone ; origin : International Flavors and Fragrances, USAl, 6-methyl-5-hepten-2-one, methyl jasmonate, methyl hexyl ketone, methyl pentyl ketone, methylnonyl ketone, cis-jasmone, Hedione ® (methyl dihydrojasmonate ; origin : Firmenich SA, Geneva, Switzerland), civettone, 4-(l,l-dimethylpropyl)-l-cyclohexanone, Exaltone ® (cyclopentadecanone ; origin : Firmenich SA, Geneva, Switzerland), 2,6,6-trimethyl-2-cyclohexene-l,4-dione, p-tert-butylcyclohexanone, tricyclo[6.2.1,02'7]undec-9-en-3-one (origin : Firmenich SA, Geneva, Switzerland), 10,10-dimethyl-tricyclo[7.1.1.02'7]undec-2-en-4-one (origin : Firmenich SA, Geneva, Switzerland), Vertofix coeur (origine : International Flavors and Fragrances, USA), la perhydro-5,5,8a-trimethyl-2-naphtalenone (origin : Firmenich SA, Geneva, Switzerland) or 5-methyl-exo-tricyclo[6.2.1.02'7]undecan-4-one.
Furthermore, it should be noted that the process of the invention is of much more general use than merely the improved perfuming of textiles treated with laundry products containing lipases. It constitutes, in fact, a general process for washing said textiles which is also advantageous whenever it is desired to improve the activity of certain agents, fragrant or other, currently present in laundry products, i.e. detergents and fabric softeners. It is well-known for instance that said laundry products are often very aggressive media, wherein a great number of perfuming ingredients, and more particularly fragrant aldehydes, turn out to be unstable and cannot therefore be used to perfume those products, nor the textiles washed therewith. The use according to the invention of the corresponding esters and enol-esters of formula (I) can obviate this problem whenever said enol-
esters turn out to be more stable. It is also quite clear that one can make use of the process of the invention to improve and prolong the action of bactericide agents, namely alcohols, whether they are fragrant or not.
Therefore, the process according to the invention is in fact a general process for treating textiles or fabrics upon the washing of the latter with a lipase-containing detergent, which washing can be followed by treatment with a fabric softener, according to which process any alcohol, aldehyde or ketone currently used in fabric detergents or softeners for its perfuming, bactericide or other activity, can be replaced by the corresponding compound (I), so as to improve its activity.
Compounds (I) are novel chemical entities and thus are also the object of the invention. Amongst said compounds, those wherein y represents a C7 to C24 linear or branched, saturated or unsaturated alkyl radical are fatty acids esters or enol-esters which do not themselves possess an interesting odour, but which, when used according to the process of the invention, are capable of imparting to the fabrics the fragrances typical of the corresponding alcohols, aldehydes and ketones defined above. Said compounds, in particular the derivatives having 12 to 16 carbon atoms, are preferred according to the invention, owing to the particularly advantageous results obtained upon their use.
As regards the compounds (I) wherein Y represents a -(CH2)nCOOR group, R being defined as above and n being an integer from 0 to 6, they are novel diesters, which are either devoid of odour, or possess odours which are not particularly useful for perfumery. However, they showed similar behaviour to that of the compounds (I) cited here-above, when used in the context of the present invention.
The compounds (I) of the invention can be added to the detergents and fabric softeners either on their own, or in admixture with other perfuming ingredients, solvents or adjuvants, of current use in perfumery. The concentrations in which they can be added to the detergents and fabric softeners according to the invention have the values usual in the art for this type of products. The skilled person is quite able to select such values as a function of the nature of the product to be perfumed and of the desired olfactive effect. By way of example, concentrations of the order of 0.01 to 1%, or even up to 5%, by weight of compound (I), relative to the weight of detergent or fabric softener composition, can be cited.
The fabric detergents and softeners according to the invention can take the form of powders or granular solids, bars, pastes or yet aqueous or
non-aqueous liquids, and contain the usual ingredients for this type of product. Thus, the detergents can typically contain, in addition to the lipase (see, for example, EP 430 315 for a detailed description of the type of lipases that can be used according to the present invention), for example active anionic, cationic, zwitterionic or non-ionic compounds, as well as filling agents, bleaching agents, confining agents and other ingredients of current use in the detergent bases intended for washing linen. A detailed description of the base detergent compositions which are adapted to be used according to the process of the invention is unwarranted here. A great many examples of such compositions can be found in the art and namely in the literature which is cited for instance in the European patent application mentioned above, or yet in European patent application EP 397 245. By way of example, a base detergent of this type, to which there is added the lipase in the desired concentration, can have the following composition (origin : Henkel KGaA, Diisseldorf, Germany) :
Ingredients % by weight
Linear sodium alkyl benzene
sulfonate (average length of the alcane chain :~Cn 5) 8.0
Ethoxylated tallow alcohol (14 EO) 2.9
Sodium soap
(chain length C12_i6 : 13-26%
C18-22 : 74-87%) 3.5
Sodium triphosphate 43.8
Sodium silicate (Si02 : Na20=3.3:l) 7.5
Magnesium silicate 1.9
Carboxymethylcellulose 1.2
Sodium ethylenediaminetetraacetate 0.2
Sodium sulfate 21.2
Water - 9.8
Total 100.0
Similar considerations apply to the fabric softener bases according to the invention, which will typically contain cationic softening ingredients of the type cited in EP 397 245 or in the literature mentioned in this reference.
The compounds of the invention can be prepared by conventional synthetic methods. For example, the derivatives of fragrant
alcohols were prepared by the esterification method summarized in the following reaction scheme :
Scheme I
(Scheme Removed)
wherein Y and R are defined as in claim 1.
The enol-esters of fragrant aldehydes and ketones were also prepared by conventional methods, starting from said aldehydes and ketones, by way of reactions of the type of those represented hereinafter :
(Formula Removed)

R1, R2 and Y are defined as in claim lb.
a) acetic anhydride ; potassium acetate; e thyl amine ; 120°; see, for example, D.P.
Simmons et al., Helv. Chim. Acta 71, 1000 (1988)
a') acetic anhydride; p-toluenesulfonic acid (cat.); 120° ; see, for example, T. Taapken et al., J. Chem. Soc. Perkin Trans. 1,1994. 1439
b) potassium tert-butoxyde; YCOC1 ; see, for example, P. Duhamel et al., J. Chem. Soc.
Perkin Trans. I, 1993. 2509
The reaction conditions are described in detail in the preparation examples presented hereinafter, wherein the temperatures are in degrees centigrade and the abbreviations have the usual meaning in the art. The invention will also be illustrated by way of application examples.
Example 1
Preparation of mono-esters General me trio d
To a stirred solution of the appropriate ROH alcohol (0.064 mole) and triethylamine (7.4 g, 0.073 mole) in CH2C12 (HO ml), there was added dropwise during 20 min, at 15° and under N2 the corresponding YC(0)C1 acyl chloride (0.07 mole), wherein Y is a C7 to C24, linear of branched, saturated or unsaturated alky] radical. After 2 h at room temperature, the mixture was poured on aq. sat. NaHCO3 (excess) and the organic phase was separated. Extraction of the aqueous phase with CHL2C12 was followed by washing of the combined organic phases with 10% aqueous NaCl. The reaction product was dried over Na2SO4, concentrated and distilled to provide the desired ester in a pure state and in 80 to 90% yield.
The following mono-esters were prepared according to the above-described general method.
a. 2-phenylethyl octanoate
B. p. 100-101°/4Pa
rR(CHCl3) : 2930, 2858, 1728, 1498, 1455, 1168, 1106 cm-l
NMR(1H, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.27(8H) ; 1.59(2H) ; 2.28(t, J=7Hz, 2H) ; 2.93(t, J=7Hz, 2H) ; 4.29(t, J=7Hz, 2H) 7.20-7.35(5H) 5 ppm.
NMR(13C) : 173.7(s) ; 138.0(s) ; 128.9(d) ; 128.5(d) ; 126.5(d) ; 64.7(t) ; 35.2(t); 34.4(t); 31.7(t) ; 29.1(t); 28.9(f); 25.0(f); 22.6(f); 14.0(q) 5 ppm.
MS : 248(0, M+), 127(2), 104(100), 57(12).
b. 2-phenylethyl hexadecanoate
M. p. 40°
IR(CHCl3) : 2927, 2855, 1728, 1456, 1174 cm-1
NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.26(24H) ; 1.58(2H) ; 2.27(t,
J=7Hz, 2H) ; 2.93(t, J=7Hz, 2H) ; 4.29(t, J=7Hz, 2H) ; 7.20-7.35(5H)
8 ppm. NMR(13C): 173.7(s); 138.0(s) ; 128.9(d); 128.5(d); 126.5(d); 64.7(t) ;
35.3(f) ; 34.4(t) ; 32.0(t) ; 29.7(2t) ; 29.5(t) ; 29.4(t) ; 29.3(f) ; 29.2(t) ;
25.0(t) ; 22.7(t) ; 14.1(q) 5 ppm.
MS : 360(0, M+), 104(100).
c 3,7-dimethyl-6-octenyl octanoate B. p. 108-109°/2.7Pa
IR(CHCl3) : 2829, 2858, 1725, 1460, 1379, 1231, 1171, 1106 cm"1 NMR(1H, 360MHz): 0.88(t, J=7Hz, 3H) ; 0.91(d, J=7Hz, 3H) ; 1.10-
1.80(15H); 1.61(s, 3H) ; 1.68(s, 3H) ; 1.98(m, 2H) ; 2.29(t, J=7Hz, 2H) ;
4.10(m, 2H) ; 5.09(broad t, J=7Hz, 1H) 5 ppm. NMR("C) : 173.9(s) ; 131.3(s) ; 124.7(d) ; 62.8(t) ; 37.1(t) ; 35.6(t) ; 34.5(t) ;
31.7(t) ; 29.6(d) ; 29.2(t) ; 29.0(t) ; 25.7(q) ; 25.5(t) ; 25.1(t); 22.6(1);
19.5(q) ; 17.7(q) ; 14.1 (q) 5 ppm. MS : 282(0, M+), 138(30), 123(56), 109(25), 95(77), 81(100), 69(59).
d. 3,7-dimethyl-6-octenyl hexadecanoate
B. p. (bulb-lo-bulb distillation) 210-230°/5.3 Pa
IR(CHC13) : 2827, 2855,1725,1465,1233,1178 cm"1
NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 0.92(d, J=7Hz, 3H) ; 1.15-
1.35(26H); 1.44(m, 1H); 1.60(s, 3H) ; 1.68(s, 3H) ; 1.50-1.70(4H) ;
1.98(m, 2H); 2.28(t, J=7Hz, 2H) ; 4.10(m, 2H) ; 5.09(broad t, J=7Hz,
1H) 5 ppm. NMR(13C) : 173.9(s) ; 131.3(s) ; 124.6(d) ; 62.8(t) ; 37.1(t) ; 35.6(t) ; 34.5(t) ;
32.0(t) ; 29.7(2t) ; 29.6(d) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 25.7(q) ;
25.5(t) ; 25.1(t) ; 22.7(t) ; 19.5(q) ; 17.7(q) ; 14.1(q) 5 ppm. MS : 394(0, M+), 138(32), 123(30), 95(60), 82(70), 69(70), 57(100).
e. 3-methyl-5-phenylpentyl octanoate
B. p. 133-135°/2.7Pa
IR(CHC13) : 2930, 2858, 1728, 1496, 1456,1231, 1171, 1106 cm"*
NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 0.98(d, J=7Hz, 3H) ; 1.28(8H) ;
1.40-1.80(7H) ; 2.27(t, J=7Hz, 2H) ; 2.62(m, 2H) ; 4.11(m, 2H); 7.10-
7.30(511) 5 ppm. NMR(!3C) : 173.9(s) ; 142.7(s) ; 128.3(2d) ; 125.7(d) ; 62.6(t) ; 38.8(t) ; 35.5(t) ;
34.4(t); 33.3(0; 31.7(0; 29.6(d); 29.2(0; 29.0(0; 25.0(0; 22.6(0;
19.5(q) ; 14.1(q) 5 ppm. MS : 304(0, M+), 160(55), 131(30), 104(100), 91(56).
£. 3-methyl-5-phenylpentyl hexadecanoate B. p. (bulb-to-bulb distillation) 250°/4 Pa
IRCCHCl3) : 2927, 2855,1727, 1456, 1235,1178 cm-1
NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 0.97(d, J=7Hz, 3tt) ; 1.26(24H) ;
1.48(2H) ; 1.55-1.80C5H) ; 2.27(t, J=7Hz, 2H) ; 2.62(m, 2H) ; 4.10(m,
2H) ; 7.15-7.30(5H) 5 ppm. NMR(13C) : 173.9(s) ; 142.6(s) ; 128.3(2d) ; 125.7(d) ; 62.6(t) ; 38.8(t) ; 35.5(t) ;
34.5(t) ; 33.3(t) ; 32.0(t) ; 29.7(2t) ; 29.7(d) ; 29.6(t) ; 29.5(t) ; 29.4(t) ;
29.3(t) ; 29.2(t); 25.1(t) ; 22.7(t) ; 19.5(q) ; 14.1(q) 5 ppm. MS : 416(0, M+), 160(43), 129(22), 115(36), 104(72), 91(68), 71(61), 57(100).
. 7-p-menthanyl octanoate (cis /trans 70:30) B. p. 105-115°/2.7Pa
ER(CHC13) : 2929, 2858,1724,1453, 1232,1172,1106 cm-1 NMR(lH, 360MHz) : cis-7 : 0.86(d, J=7Hz, 6H) ; 0.88(t, J=7Hz, 6H) ; 2.30(t, J=7Hz, 2H) ; 4.02(d, J=7Hz, 2H) 8 ppm.
trans-7 : 2.30(t, J=7Hz, 2H) ; 3.88(d, J=7Hz, 2H) 5 ppm. NMR(!3C) : cis-7 : 174.0(s) ; 66.6(t) ; 43.0(d) ; 34.5(t) ; 33.9(d) ; 30.6(d) ; 29.9(t) ; 29.2(t) ; 29.1(t) ; 26.5(t) ; 25.6(0 ; 25.1(t) ; 20.3(q) ; 14.0(q) 5 ppm.
trans-7 : 174.0(s) ; 69.5(t) ; 44.1(d) ; 37.5(d) ; 32.9(d) ; 31.7(t) ; 22.6(t) ; 19.8(q) ; 14.0(q) 5 ppm. MS : cis-7 : 282(0, M+), 138(23), 123(17), 109(35), 95(100), 81(27).
trans-7 : 282(0, M+), 138(27), 123(17), 109(22), 95(100), 81(35).
. 9-decenyl octanoate B. p. 120-121O/2.7 Pa
IR(CHC13) : 2830, 2857, 1725, 1466, 1171 cm-1 NMR(1H, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.30(18H); 1.61 (4H) ; 2.04(broad q,
J=7Hz, 2H); 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d,
J=HHz, 1H) ; 4.99(broad d, J=17Hz, 1H) ; 5.80(m, 1H) 8 ppm. NMR(13C) : 173.9(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 33.8(t) ; 31.8(t) ;
29.4(t) ; 29.3(t) ; 29.2(t) ; 29.1(t) ; 29.0(2t) ; 28.8(t) ; 26.0(t) ; 25,l(t) ;
22.7(t) ; 14.1(q) 8 ppm. MS : 282(0, M+), 145(38), 109(38), 96(86), 82(89), 68(91), 55(100).
9-decenyl nonanoate B. p. (bulb-to-bulb distillation) 130-160°/2.7 Pa
NMR(lH, 360MHz) : 0.88(1:, J=7Hz, 3H) ; 1.20-1.45(20H) ; 1-61 (4H) ; 2.04
(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ;
4.93(broad d, J=llHz, 1H) ; 4.99(broad d, J=17Hz, 1H) ; 5.80(m, 1H)
5 ppm. NMR(«C) : 174.0(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 33.8(t) ; 31.9(t) ;
29.4(0 ; 29.3(t) ; 29.2(2t) ; 29.1(t) ; 29.0(t) ; 28.7(t) ; 26.0(t) ; 25.1(0 ;
22.7(t) ; 14.1(q) 5 ppm. MS : 296(0, M+), 159(27), 138(28), 96(100), 82(75), 68(73), 55(83).
j. 9-decenyl decanoate B. p. 144-145°/2.7Pa
IR(CHC13): 2929, 2856 1726,1466,1178 cm-1 NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H); 1.30(22H) ; 1.61(4H) ; 2.04(broad q,
J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.05(t, J=7Hz, 2H) ; 4.93(broad d,
J=llHz, 1H) ; 4.98(broad d, J=17Hz, 1H); 5.80(m, 1H) 5 ppm. NMR(13C) : 173.9(s) ; 139.1(d); 114.2(0 ; 64.4(0 ; 34.5(0 ; 33.8(0 ; 31.9(0 ;
29.5(0 ; 29.3(0 ; 29.2(t) ; 29.1(0 ; 29.0(0 ; 28.7(0 ; 26.0(0 ; 25.1(0 ;
22.7(0 ; 14.1 (q) 5 ppm. MS : 310(0, M+), 138(33), 109(29), 96(100), 82(82), 68(98).
k. 9-decenyl undecanoate
B. p. (bulb-to-bulb distillation) 130-150°/20 Pa
NMR(lH, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.20-1.45(24H) ; 1.61(4H) ;
2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ;
4.93(broad d, J=llHz, 1H); 4.99(broad d, J=17Hz, 1H); 5.81(m, 1H)
5 ppm. NMR(13C) : 173.9(s) ; 139.1(d); 114.2(0 ; 64.4(0 ; 34.5(0 ; 33.8(0 ; 32.0(0 ;
29.6(20 ; 29.4(20 ; 29.3(0 ; 29.1(0 ; 29.0(0 ; 28.8(0 ; 26.0(0 ; 25.1(0 ;
22.7(t) ;14.1(q) 5 ppm. MS : 324(0, M+), 187(20), 138(43), 109(33), 96(100), 82(96), 68(89), 55(91).
1. 9-decenyl dodecanoate
B. p. 164-165°/4Pa
IR(CHCl3) : 2928, 2856, 1726, 1216 cm'1
NMR(lH, 360MHz) : 0.89(t, J=7Hz, 3H) ; 1.28(26H); 1.62(4H) ; 2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d, J=HHz, 1H) ; 4.98(broad d, J=17Hz, 1H) ; 5.80(m, 1H) 5 ppm.
NMR(13Q : 174.0(s) ; 139.2(d) ; 114.2(t); 64.4(t); 34.5(t) ; 33.8(t) ; 32.0(t) ;
29.6(t) ; 29.5(t) ; 29.4(2t) ; 29.3(t) ; 29.2(t) ; 29.1(2t) ; 28.9(t) ; 28.7(t) ;
26.0(t); 25.1 (t); 22.7(t); 14.1 (q) 5 ppm. MS : 338(0, M+), 138(48), 109(35), 96(100), 82(96), 68(89), 55(98).
• 9-decenyl tridecanoate B. p. (bulb-to-bulb distillation) 150-175°/13 Fa NMR(1H, 360MHz): 0.88(t, J=7Hz, 3H) ; 1.20-1.45(28H) ; 1.61 (4H) ;
2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.05(t, J=THz, 2H);
4.93(broad d, J=HHz, 1H) ; 4.99(broad d, J=17Hz, 1H) ; 5.81(m, 1H)
5 ppm. NMR(13C) : 174.0(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 33.8(t) ; 32.0(t) ;
29.7(t) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 29.1(t) ; 29.0(t) ; 28.7(t) ;
26.0(t) ; 25.1(t) ; 22.7(t) ; 14.1(q) 5 ppm. MS : 352(0, M+), 138(52), 110(41), 96(99), 82(83), 68(93), 55(100).
9-decenyl t£tradecanoate B. p. (bulb-to-bulb distillation) 200-220°/4 Pa NMR(1H, 360MHz) : 0.88(t, J=7Hz, 3H) ; 1.28(30H) ; 1.62(4H) ; 2.04(broad q,
J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ; 4.93(broad d,
J=llHz, 1H); 4.99(broad d, J=17Hz, 1H) ; 5.81 (m, 1H) 5 ppm. NMR(13C : 174.0(s) ; 139.1(d) ; 114.2(t) ; 64.4(t) ; 34.5(t) ; 34.5(t) ; 33.8(t) ;
32.0(t) ; 29.7(t) ; 29.5(t) ; 29.4(t) ; 29.3(2t); 29.1(t) ; 29.0(t) ; 28.7(t) ;
26.0(t) ; 25.1(t) ; 22.7(t) ; 14.1(q) 5 ppm. MS : 366(0, M+), 138(52), 110(47), 96(100), 82(96), 55(96).
9-decenyl pentadecanoate
B. p. (bulb-to-bulb distillation) 175-210°/13 Pa NTMR(1H, 360MHz): 0.88(t, J=7Hz, 3H) ; 1.20-1.45(32H) ; 1.62(4H) ;
2.04(broad q, J=7Hz, 2H) ; 2.29(t, J=7Hz, 2H) ; 4.06(t, J=7Hz, 2H) ;
4.93(broad d, J=llHz, 1H); 4.99(broad d, J=17Hz, 1H) ; 5.81(m, 1H)
5 ppm. NMR(13C) : 174.0(s) ; 139.1(d) ; 114.2(t); 64.4(t); 34.5(t) ; 33.8(t) ; 32.0(t) ;
29.7(2t) ; 29.5(t) ; 29.4(t) ; 29.3(t) ; 29.2(t) ; 29.1(t) ; 29.0(t) ; 28.7(t) ;
26.0(t) ; 25.1(t) ; 22.7(t) ; 14.1 (q) 5 ppm. MS : 380(0, M+), 138(50), 110(30), 96(100), 82(85), 68(79), 55(80).
p. 9-decenyl hexadecanoate
NMR1H, 360MHz) : 5.84(111, 1H) ; 4.95(m, 2H) ; 4.05(t, 2H) ; 3.73(q, 4H) ;
2.31 (t, 2H) ; 2.05(broad q, 2H) ; 1.61(m, 4H); 1.2-1.4(broad m, 30H);
0.89(111, 3H) 5 ppm. NMR(13C) : 14.12(q) ; 18.44(q) ; 22.72(t) ; 25.06(t) ; 25.95(t) ; 28.68(t) ;
28.92(t); 29.05(t); 29.21 (t) ; 29.30(t) ; 29.39(t) ; 29.51 (t) ; 29.64(t) ;
29.71(t) ; 31.95(t) ; 33.80(t) ; 34.45(t) ; 58.45(t) ; 64.41 (t) ; 114.17(t) ;
139.16(d) ; 174.07(s) 5 ppm. MS : 394(0, M+), 96(72), 83(70), 82(88), 55(100).
q. 1-methylpentyl hexadecanoate
NMR(1H 360MHz) : 4.90(m, 1H) ; 2.26(t, 2H) ; 1.65(m, 4H) ; 1.25-1.32(m,
28H) ; 1.20(d, 3H); 0.89(q, 6H) 5 ppm. NMR(13C) : 13.97(q) ; 14.00(q) ; 20.40(q) ; 22.56(t) ; 22.7(t) ; 25.1 (t) ; 27.6(t) ;
29.2(t) ; 29.3(t) ; 29.4(t); 29.5(t) ; 29.6(t) ; 29.7(t) ; 29.73(t) ; 31.97(t);
34.83(t) ; 35.75(t) ; 70.74(d); 173.50(s) 5 ppm. MS : 84(100), 69(50), 57(70), 55(62), 43(98).
r. 7-p-menthanyl hexadecanoate
NMR(lH, 360MHz) : 0.80-0.95(m, 9H) ; 1.2-2.0(broad m, 37H) ; 2.32(t, 2H) ;
3.88 et 4.02(d, 2H) 5 ppm. NMR(13C) : 14.09(t) ; 19.8(t) ; 20.2(t) ; 22.7(t) ; 25.12(t) ; 22.56(t) ; 26.44(t);
29,10(t); 29.22(t); 29.30(t) ; 29.38(t) ; 29.51 (t) ; 29.63(t) ; 29.71 (t) ;
29.92(t) ; 30.54(d) ; 31.97(t) ; 32.90(d) ; 33.90(d) ; 34.50(t) ; 37.50(d) ;
42.98(d) ; 44.11(d) ; 66.62(t) ; 69.50(t) ; 174.05(s) 5 ppm. MS : 93(70), 77(33), 69(100), 43(48), 41(92).
s. hexyl hexadecanoate
NMR(lH, 360MHz): 4.02(t, 2H) ; 3.86(broad q, 2H) ; 2.29(t, 2H) ;
1.60(broad m, 4H) ; 1.2-1.4(broad m, 28H) ; 0.90(m, 6H) 5 ppm. NMRC13C) : 14.1(q) ; 13.97(q) ; 22.58(t) ; 22.74(t) ; 25.11(t) ; 25.68(0 ; 28.75(0 ;
29.24(0; 29.34(0; 29.41(0; 29.54(0; 29.67(0; 29.72(0; 29.74(0;
31.51(0 ; 32.00(0 ; 34.50(0 ; 58.42(0 ; 64.46(0 ; 174.07(s) 5 ppm. MS : 340(2, M+), 84(100), 57{55), 56(5S), 43(80).
t. (Z)-3-hexenyl hexadecanoate
NMR(1H, 360MHz) : 5.45(m, 1H) ; 5.26(m, 1H) ; 4(t, 2H) ; 3.42(s, 4H) ; 2.2-
3.3(111, 8H) ; 2.0(m, 1H) ; 1.6(m, 8H) ; 1.2(broad m, 30H) ; 0.8-1.0(m,
6H) 5 ppm. NMR(13C): 14.14(q); 14.24(q); 20.63(t) ; 22.73(t) ; 25.02(t) ; 25.59(0;
26.37(t); 26.72(0; 26.82(0; 29.20(0; 29.32(0; 29.40(0; 29.51(0;
29.73(0 ; 31.97(0 ; 34.39(0 ; 93.77(0 ; 123.83(d) ; 134.50(d) ; 173.93(s)
5 ppm. MS : 83(25), 82(100), 67(38), 55(27), 43(14).
u- (E)-3,7-dimethyl-2,6 octadienyl hexadecanoate
NMR(1H, 360MHz) : 0.87(t, 3H) ; 1.26(m, 26H) ; 1.6(s, 3H) ; 1.68(s, 3H) ;
1.70(s, 3H) ; 2.0-2.15(m, 4H) ; 2.30(t, 2H) ; 4.6(d, 2H) ; 5.09(t, 1H) ;
5.35(t, 1H) 8 ppm. NMR(13C) : 14.12(q); 16.48(q) ; 17.69(q) ; 27.73(0; 25.08(0; 25.68(0;
26.38(0 ; 29.22(0 ; 29.33(0 ; 29.41(0 ; 29.53(0 ; 29.67(0 ; 29.72(0 ;
31.99(0 ; 34.45(0 ; 35.59(0 ; 61.19(0 ; 116.60(d) ; 123.85(d) ; 131.80(s);
142.06(s); 173.91 (s) 8 ppm. MS : 392(0, M+), 93(94), 69(100), 43(89), 41(70).
Example 2 Preparation de di-esters General method
The same method as that described in Example 1 was used, but employing
half the molar amounts of the coIResponding diacyl dichloride [(CH2)n[C(0)Cl]2, n=0 to 6].
The following di-esters were prepared according to this general method :
a. bis(9-decenyl) oxalate
B. p. (bulb-to-bulb distillation): 200°/40 Pa
m(CHCl3) : 2930, 2860, 1770, 1740,1460, 1312,1175, 912 cm-1
NMR(1H, 360MHz) : 1.25-1.45(20H) ; 1.74(m, 4H) ; 2.04(broad q, J=7Hz,
4H) ; 4.28(t, J=7Hz, 4H) ; 4.93(broad d, J=llHz, 2H) ; 4.99(broad d,
J=17Hz, 2H) ; 5.80(m, 2H) 8 ppm.
NMR(13C) : 158.1(s) ; 139.0(d) ; 114.2(t) ; 67.1(t) ; 33.8(0 ; 29.3(0 ; 29.1(t) ;
29.0(t); 28.9(t); 28.3(0 ; 25.7(0 5 ppm. MS : 366(0, M+), 138(9), 109(13), 96(27), 83(55), 69(45), 55(100).
bis(9-decenyl) malonate
B. p. (bulb-to-bulb distillation): 210°/40 Pa
IR(CHC13) : 2940, 2862,1740,1465, 1336,1276,1155, 915 cm-1
NMR(1H, 360MHz) : 1.25-1.45(20H) ; 1.64(m, 4H); 2.04(broad q, J=7Hz,
4H); 3.37(s, 2H) ; 4.14(t, J=7Hz, 4H); 4.93(broad d, J=llHz, 2H) ; 4.99
(broad d, J=17Hz, 2H) ; 5.81(m, 2H) 5 ppm. NMR(13C) : 166.6(s) ; 139.1(d) ; 114.2(t) ; 65.6(0 ; 41.7(0 ; 33.8(0 ; 29.4(0 ;
29.2(t) ; 29.1(0 ; 28.9(0 ; 28.5(0 ; 25.8(0 5 ppm. MS : 380(0, M+), 138(25), 109(21), 105(42), 96(60), 83(100), 68(65), 55(95).
bis(9-decenyl) butanedioate
IR(CHC13) : 2935, 2860,1735, 1460,1160, 995, 910 crIR-1 NMR(1H, 360MHz) : 1.25-1.45(20H); 1.63(m, 4H) ; 2.04(broad q, J=7Hz,
4H) ; 2.62(s, 4H) ; 4.08(t, J=7Hz, 4H) ; 4.93(broad d, J=llHz, 2H) ;
4.99(broad d, J=17Hz, 2H) ; 5.81 (m, 2H) 8 ppm. NTMR(13C) : 172.3(s) ; 139.1(d) ; 114.2(t) ; 64.9(0 ; 33.8(0 ; 29.4(0 ; 29.3(0 ;
29.2(t) ; 29.1(0 ; 28.9(0 ; 28.7(t) ; 25.9(0 5 ppm. MS : 394(0, M+), 138(10), 119(22). 101(60), 97(38), 83(100), 69(44), 55(76).
bis(9-decenyl) pentanedioate
IR(CHC13) : 2940, 2880,1740,1464,1180,1000, 918 cm-1 NMR0H, 360MHz) : 1.25-1.45(20H) ; 1.62(m, 4H) ; 1.95(t, J=7, 7Hz, 2H) ;
2.04(broad q, J=7Hz, 4H) ; 2.37(t, J=7Hz, 4H); 4.06(t, J=7Hz, 4H);
4.93(broad d, J=llHz, 2H) ; 4.99(broad d, J=17Hz, 2H) ; 5.81 (m, 2H)
5 ppm. NMR(13C) : 173.0(s) ; 139.1(d) ; 114.2(0 ; 64.6(0 ; 33.8(0 ; 33.4(0 ; 29.4(0 ;
29.2(0 ; 29.1(0 ; 28.9(0 ; 28.7(t); 25.9(0 5 ppm. MS : 408(0, M+), 115(100), 97(14), 87(20), 83(26), 69(19), 55(39).
bis(9-decenyl) hexanedioate
m(CHCl3) : 2942, 2864,1740,1466,1180,1000, 918 cm-1 NMR(1H, 360MHz) : 1.25-1.45(20H) ; 1.55-1.75(8H) ; 2.04(broad q, J=7Hz,
4H) ; 2.32(m, 4H) ; 4.06(t, J=7Hz, 4H) ; 4.93(broad d, J=llHz/ 2H) ;
4.99(broad d, J=17Hz, 2H) ; 5.81(m, 2H) 5 ppm.
NMR(13C) : 173.4(s) ; 139.1(d) ; 114.2(t) ; 64.5(t); 34.0(t) ; 33.8(t) ; 29.4(t) ;
29.2(t); 29.0(t); 28.9(t) ; 28.7(t); 25.9(t); 24.5(t) 5 ppm. MS : 422(0, M+), 129(90), 111(64), 101(31), 95(23), 83(60), 67(41), 55(100).
£ (E,E)-bis(3,7-dimethyl-2,6-octadienyl) oxalate IR(CHC13) : 2929, 1740, 1449, 1378, 1302, 1168 cm-1 NMR(lH, 360MHz) : 1.60(s, 6H) ; 1.68(s, 6H) ; 1.75(s, 6H) ; 2.09(8H) ; 4.80(d,
J=7Hz, 4H) ; 5.07(m, 2H) ; 5.41 (broad t, J=7Hz, 2H) 5 ppm. NMR(13C) : 158.0(s) ; 144.3(s) ; 132.0(s) ; 123.6(d) 116.9(d) ; 63.8(t) ; 39.6(t) ;
26.2(t) ; 25.7(q) ; 17.7(q) ; 16.6(q) 5 ppm. MS : 362(0, M+), 135(7), 93(20), 81(29), 69(100).
g. (E,E)-bis(3,7-dimethyl-2,6-octadienyl) malonate
IR(CHC13) : 2930,1728,1447,1379,1278,1149, 983 cm-1
NMR(1H, 360MHz) : 1.60(s, 6M) ; 1.69(s, 6H) ; 1.71(s, 6H); 2.08(8H) ; 3.38(s,
2H) ; 4.65(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.34(broad t, J=7Hz, 2H)
8 ppm. MMR(13C) : 166.6(s) ; 142.9(s) ; 131.9(s) ; 123.7(d) ; 117.8(d); 62.4(t) ; 41.7(t);
39.6(t) ; 26.4(t) ; 25.7(q) ; 17.7(q) ; 16.5(q) 5 ppm. MS : 376(0, M+), 136(17), 121(15), 93(39), 81(33), 69(100).
h. (E,E)-bis(3,7-dimethyl-2,6-octadienyl) butanedioate IR(CHC13) : 2930,1729,1446,1384,1231,1162 cm-1 NMR(lH, 360MHz) : 1.61(s, 6H) ; 1.69(s, 6H) ; 1.70(s, 6H) ; 2.08(8H) ; 2.64(s,
4H) ; 4.62(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.34(broad t, J=7Hz, 2H)
5 ppm. NTMR(13C) : 172.3(s) ; 142.3(s) ; 131.8(s) ; 123.8(d) ; 118.3(d) ; 61.7(t) ; 39.6(t) ;
29.3(t) ; 26.4(t) ; 25.7(q) ; 17.7(q) ; 16.5(q) 5 ppm. MS : 390(0, M+), 136(17), 121(19), 93(62), 81(27), 69(100).
i- (E,E)-bis(3,7-dimethyl-2,6-octadienyl) pentanedioate IR(CHCl3) : 2930, 1727, 1450, 1232, 1176 cm-1 NMR(lH, 360MHz) : 1.61(s, 6H) ; 1.68(s, 6H) ; 1.70(s, 611) ; 1.96(m, 2H) ;
2.07(8H) ; 2.37(t, J=7Hz, 4H) ; 4.59(d, J=7Hz, 4H) ; 5.08(m, 2H) ;
5.33(broad t, J-7Hz, 2H) 5 ppm. NMR(13C) : 172.9(s) ; 142.2(s) ; 131.8(s) ; 123.8(d) ; 118.4(d) ; 61.4(t) ; 39.6(t) ;
33.4(t); 26.3(t) ; 25.7(q); 20.3(t); 17.7(q); 16.5(q) 5 ppm. MS : 404(0, M+), 136(20), 121(18), 93(55), 81(48), 69(100).
j. (E,E)-bis(3,7-dimethyl-2.6-octadienyl) hexanedioate IR(CHC13) : 2931, 1727, 1446, 1384, 1233, 1174 cm-1
NMROH, 360MHZ): 1.60(S, 6H); 1.68(4H) ; 1.68(s, 6H) ; 1.70(6H) ;
2.07(8H) ; 2.33(4H) ; 4.59(d, J=7Hz, 4H) ; 5.08(m, 2H) ; 5.33(broad t,
J=7Hz, 2H) 5 ppm. NTMR(13C) : 173.3(s) ; 142.2(s); 131.8(s) ; 123.8(d) ; 118.4(d) ; 61.3(t) ; 39.8(t) ;
34.0(t) ; 2.6Ait) ; 25.7(q) ; 24.5(t) ; 17.7(q) ; 16.5(q) d ppm. MS : 418(0, M+), 135(15), 121(15), 93(52), 81(32), 69(100).
Example 3
Preparation of enol-esters General method
A 500 ml three-neck flask under argon was charged with 0.162 mole of the appropriate aldehyde of formula
(Formula Removed)
2.5 g (26 mmole) of anhydrous potassium acetate, 34.45 g (0.34 mole) of triethylamine and 250 ml of acetic anhydride. After heating for 6 h at 120°, the reaction mixture was cooled to room temperature, poured on ice, extracted three times with petroleum ether 30-50°, washed 6 times with 100 ml of saturated NaHCO3, then with water to neutrality. After drying over Na2SO4, filtering, concentrating under vacuum and distilling on a Vigreux column, there was obtained the enolacetate coIResponding to the starting aldehyde, in the form of a mixture of E and Z isomers. The latter were then separated by preparative gas chromatography. When starting from a ketone of formula
(Formula Removed)
there was followed a method analogous to that described by T. Taapken et al., J. Chem. Soc. Perkin Trans. I, 1994, 1439, wherein the ketone is dissolved
in the acetic anhydride and treated with p-toluenesulfonic acid as catalyst, and the formed acetic acid is eliminated to obtain the coIResponding enolacetate.
The enolacetates thus prepared are then converted into the enol-esters of formula (I) proceeding as follow.
'"A 500 ml three-neck flask under argon was charged with 0.05 mole of enolacetate and 75 ml of absolute tetrahydrofuran. The mixture was cooled to -60/-700 (dry ice/acetone bath) and a solution of 6.16 g (0.055 mole) of t-BuOK in 60 ml of absolute THF was introduced dropwise (slightly exothermic, the reaction mixture becomes strongly yellow). StiIRing was kept for 1 h at -70° and 0.055 mole of the appropriate acyl chloride, in solution in 25 ml of absolute THF, were added dropwise. After 2 h at -70°, the cooling bath was removed and 60 ml of a saturated solution of NaHCO3 were quickly added (the temperature rises quickly to -10°). The mixture was extracted twice with sulfuric ether, washed once with saturated NaHCO3, once with water satured with salt, dried (Na2SO4) and concentrated under vaccum. The product is then purified by flash-chromatography (column diameter = 9 cm, hexane/ether 98:2) and, after combining the useful layers, concentrated to dry under absolute vaccum. According to this method, there were prepared the following enol-esters :
a. 2-(4-tert-butylbenzyl)-l-propenyl acetate Isomer (Z) NMR(1H, 360MHZ, CDC13) : 1.32(s, 9H) ; 1.59(s, 3H) ; 2.16(s, 3H) ; 3.43(s,
2H) ; 6.99(broad s, 1H) ; 7.10(d, J=8, 2H) ; 7.31 (d, J=8, 2H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 17.4(q) ; 20.8(q); 31.4(q) ; 31.4(q) ; 31.4(q) ;
35.3(t) ; 125.3(d) ; 125.3(d) ; 128.3(d) ; 128.3(d) ; 130.5(d) ; 34.4(s) ;
121.2(s) ; 136.0(s) ; 149.0(s) ; 168.3(s) 5 ppm. MS : 246(13, M+); m/e, 204(17), 189(73), 171(7), 159(8), 147(31), 129(33),
119(100), 105(9), 91(40), 77(8), 71(7), 57(60), 43(64).
Isomer (E)
NMR(lH, 360MHz, CDCI3) : l-32(s, 9H) ; 1.62(s, 3H) ; 2.15(s, 3H) ; 3.24(s,
2H) ; 7.05(broad s, 1H) ; 7.12(d, J=8, 2H) ; 7.31 (d, J=8, 2H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 13.6(q) ; 20.8(q) ; 31.4(q) ; 31.4(q) ; 31-4(q) ;
39.8(t); 125.3(d); 125.3(d); 128.4(d); 128.4(d); 131.2(d); 34.4(s) ;
121.4(s) ; 135.9(s) ; 149.2(s) ; 168.3(s) 5 ppm. MS : 246(12, M+); m/e, 204(41), 189(100), 171(3), 159(7), 147(42), 131(21),
119(57), 105(9), 91(32), 77(6), 71(8), 57(45), 43(58).
b. 3,7-dimethyl-l ,6-octadienyl acetate
The analytical characteristics of this compound were identical to those published in the literature (see, D.P. Simmons et al., ref. cited).
c 3,7-dimethyl-l ,6-octadienyl octanoate Isomer (Z) NMR(1H, 360MHZ, CDCI3) : 0.89(t, J=7, 3H) ; 0.99(d, J=7, 3H) ; 1.30(m,
10H) ; 1.59(s, 3H) ; 1.68(s, 3H) ; 1.94(m, 2H) ; 2.39(t, J=7, 2H) ; 2.68(m,
1H) ; 4.67(dd, Ji=6, J2=10, 1H) ; 5.10(m, 1H); 7.00(d, J=6,1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1(q) ; 17.6(q) ; 20.9(q) ; 25.7(q) ; 22.6(t) ;
24.8(t) ; 25.9(t) ; 28.9(t) ; 29.0(t) ; 31.7(t) ; 34.2(t) ; 37.4(t) ; 29.4(d) ;
120.1(d) ; 124.5(d) ; 133.1(d) ; 131.3(s) ; 171.0(s) 5 ppm. MS : 280(0, M+); m/e, 198(1), 182(2), 154(8), 136(35), 127(100), 121(30),
109(20), 93(12), 82(17), 69(23), 57(96), 41(32).
Isomer (E)
NMR^'H, 360MHz, CDCI3) : 0.89(t, J=7, 3H) ; 1.02(d, J=7, 3H) ; 1.30(m,
10H) ; 1.59(s, 3H) ; 1.68(s, 3H) ; 1.96(m, 2H) ; 2.15(m, 1H) ; 2.36(t, J=7,
2H) ; 5.07(m, 1H); 5.29(dd, Ji=8, J2=12,1H)_; 7.08(d, J=12,1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1(q) ; 17.7(q) ; 20.9(q) ; 25.7(q) ; 22.6(t) ;
24.7(t) ; 25-7(t) ; 28.9(t) ; 29.1(t) ; 31.6(t) ; 34.1 (t) ; 37.2(t) ; 32.0(d) ;
120.4(d) ; 124.3(d) ; 134.6(d) ; 131.5(s) ; 171.2(s) 5 ppm. MS : 280(0, M+); m/e, 198(1), 185(1), 154(7), 136(32), 127(93), 121(26),
109(19), 93(11), 82(15), 69(23), 57(100), 41(32).
d. 2-methyl-l-undecenyl acetate Isomer (Z) NMR(!H, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.27(m, 12H) ; 1.39(m, 2H);
1.63(split s, 3H) ; 2.11(m, 2H) ; 2.13(s, 3H); 6.83(broad s, 1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1(q) ; 17.4(q) ; 20.7(q) ; 22.7(t) ; 27.0(t) ; 29.3-
29.6(t) ; 29.3-29.6(t) ; 29.3-29.6(t) ; 29.3-29.6(0 ; 29.3-29.6(t) ; 31.9(t) ;
120.0(d) ; 122.3(s); 168.3(s) 5 ppm. MS : 226(3, M+); m/e, 184(33), 166(1), 141(2), 124(3), 110(6), 95(14), 82(15),
71(100), 57(13), 43(50).
Isomer (E)
NMR(1H/ 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.27(m, 12H) ; 1.40(m, 2H) ; 1.66(split s, 3H) ; 1.95(m, 2H); 2.13(s, 3H); 6.88(broad s, 1H) 5 ppm.
NMR(13C, 90MHz, CDCI3) : 13.6(q) ; 14.1(q) ; 20.8(q) ; 22.7(0 ; 27.6(t) ;
29.2(0 ; 29.3(0 ; 29.5(t) ; 29.6(t) ; 31.9(t); 33.9(t) ; 130.2(d) ; 122.0(s);
168.3(s) 5 ppm. MS : 226(2, M+); m/e, 184(25), 166(1), 141(2), 123(3), 110(5), 95(12), 81(18),
71(100), 58(9), 43(40).
e. 2-methyl-l-undecenyl octanoate Isomer (Z) NMR(lH, 360MHz, CDCI3) : 0.88(t, J=7, 6H) ; 1.27(m, 22H) ; 1.39(m, 2H) ;
1.52(split s, 3H) ; 2.10(t, J=7, 2H) ; 2.37(t, J=7, 2H) ; 6.85(broad s, 1H)
8 ppm. NMR(13C, 90MHz, CDCI3) : 14.0(q) ; 14.1(q) ; 17.4(q) ; 22.6(t) ; 22.7(t) ;
24.9(t) ; 27.1(t) ; 28.9-29.6(0 ; 28.9-29.6(t) ; 28.9-29.6(t) ; 28.9-29.6(0 ;
28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 31.7(0 ; 31.9(0 ; 34.2(0 ;
129.9(d) ; 122.2(s) ; 171.l(s) 5 ppm. MS : 310(0, M+); m/e, 184(10), 127(85), 109(10), 95{6\ 81(10), 71(25), 57(100),
43(10).
Isomer (E)
NMR(1H, 360MHz, CDCI3) : 0.88(t, J=7, 6H) ; 1.27(m, 22H) ; 1.40(m, 2H);
1.67(split s, 3H) ; 1.95(t, J=7, 2H) ; 2.39(t, J=7, 2H) ; 6.89(broad s, 1H)
5 ppm. NMR^SC, 90MHz, CDCI3) : 13.6(q) ; 14.0(q) ; 14.1 (q) ; 22.6(0; 22.7(0;
24.9(0 ; 27.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ; 28.9-29.6(0 ;
28.9-29.6(0 ; 28.9-29.6(0 ; 31-7(0 ; 31.9(0 ; 34.0(t) ; 34.2(0 ; 130.1(d);
121.9(s) ; 171.l(s) 5 ppm. MS : 310(0, M+); m/e, 184(10), 127(87), 109(10), 97(7), 81(13), 71(28), 57(100),
43(9).
f. 1-undecenyl acetate Isomer (Z) NTMR(1H, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.28(m, 12H) ; 1.37(m, 2H) ;
2.12(m, 2H); 2.14(s, 3H) ; 4.87(dt, J1=J2=6, 1H) ; 6.99(d, J=6, 1H)
5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1 (q) ; 20.8(q) ; 22.7(0 ; 24.4(0 ; 29.2-29.6(0 ;
29.2-29.6(0 ; 29.2-29.6(0 ; 29.2-29.6(0 ; 29.2-29.6(0 ; 31.9(0 ; 114.4(d) ;
134.0(d) ; 168.2(s) 5 ppm.
MS : 212(0, M+); m/e, 170(1), 152(3), 124(5), 110(6), 96(26), 82(34), 68(18), 57(33), 43(100).
Isomer (E)
NMROH, 360MHz, CDC13) : 0.88(t, J=7, 3H) ; 1.27(m, 12H) ; 1.37(m, 2H) ;
1.99(q, J=7, 2H) ; 2.11(s, 3H) ; 5.41(dt, Ji=7, J2=12, 1H) ; 7.06(d, J=12,
1H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 14.1 (q) ; 20.7(q) ; 22.7(0 ; 27.3(t) ; 29.1-29.6(0 ;
29.1-29.6(t) ; 29.1-29.6(0 ; 29.1-29.6(0 ; 29.1-29.6(0 ; 31.9(0 ; 115.1(d) ;
135.4(d) ; 168.3(s) 5 ppm. MS : 212(0, M+); m/e, 170(1), 152(4), 124(7), 110(8), 96(34), 82(41), 68(19),
57(39), 43(100).
3-methyl-5-phenyl-l-pentenyl acetate
Isomer (Z)
NTMR(1H, 360MHz, CDCI3) : 1.02(d, J=7, 3H) ; 1.54(m, 1H) ; 1.69(m, 1H) ;
2.10(s, 3H) ; 2.48-2.78(m, 311) ; 4.72(dd, Ji=6, J2=10, 1H) ; 7.03(d, J=6,
1H) ; 7.17(m, 3H) ; 7.26(m, 2H) 5 ppm. NTMR(13C, 90MHz, CDCI3) : 20.7(q) ; 21.0(q) ; 33.7(0 ; 38.9(0 ; 29.2(d) ;
119.8(d) ; 125.6(d) ; 128.2(d) ; 128.2(d) ; 128.4(d) ; 128.4(d) ; 133.4(d) ;
142.5(s) ; 168.1 (s) 5 ppm. MS : 218(1, M+); m/e, 176(3), 158(39), 143(27), 131(10), 117(6), 104(16),
91(45), 71(43), 65(13), 51(7), 43(100).
Isomer (E)
NMR(lH, 360MHz, CDCI3) : 1.06(d, J=7, 3H) ; 1.62(m, 2H) ; 2.12(s, 3H);
2.18(m, 1H) ; 2.60(m, 2H) ; 5-33(dd, Ji=9, J2=13, 1H) ; 7.09(d, J=13,
1H) ; 7.17(m, 3H) ; 7.27(m, 2H) 5 ppm. NMR(13C, 90MHz, CDCI3) : 20.7(q) ; 21.0(q) ; 33.5(0 ; 38.8(t) ; 32.1(d) ;
120.3(d) ; 125.7(d) ; 128.3(d) ; 128.3(d); 128.4(d) ; 128.4(d) ; 134.9(d) ;
142.3(s) ; 168.3(s) 5 ppm. MS : 218(1, M+); m/e, 176(4), 158(34), 143(25), 131(9), 117(5), 104(16), 91(44),
71(48), 65(12), 51(6), 43(100).
3-methyl-5-phenyl-l -pentenyl octanoate
Isomer (Z)
KTMROH, 360MHz, CDCI3) : 0.89(t, J=7, 3H) ; 1.02(d, J=7, 3H) ; 1.30(m, 8H) ; 1.49-1.76(m, 4H) ; 2.36(t, J=7, 2H) ; 2.48-2.78(m, 3H) ; 4.72(dd, Jl=7, J2=10, 1H) ; 7.05(d, J=7, 1H) ; 7.17(m, 3H) ; 7.26(m, 2H) 5 ppm.
NTMR03C, 90MHz, CDCI3) : 14.1(q) ; 21.0(q) ; 22.6(t) ; 24.7(t) ; 28.9(t) ;
29.0(t); 31.7(0 ; 33.7(0 ; 34.1(t) ; 38.9(0 ; 29.3(d); 119.7(d) ; 125.6(d);
128.2(d) ; 128.2(d) ; 128.4(d) ; 128.4(d) ; 133.4(d) ; 142.5(s) ; 171.0(s)
S ppm. MS : 308(0, M+); m/e, 176(8), 158(78), 143(18), 127(100), 104(36), 91(51),
71(10), 57(71), 43(14).
Isomer (E)
NMROH, 360MHz, CDCI3) : 0.89(t, J=7, 3H) ; 1.07(d, J=7, 3H) ; 1.30(m,
8H) ; 1.65(m, 4H) ; 2.18(m, 1H) ; 2.37(t, J=7, 2H) ; 2.60(m, 2H) ;
5.33(dd, J1=8, J2=12, 1H) ; 7.10(d, J=12, 1H) ; 7.17(m, 3H) ; 7.27(m, 2H)
8 ppm. NTMR(13C, 90MHz, CDCI3) : 14.1(q) ; 21.0(q) ; 22.6(t) ; 24.7(t) ; 28.9(0 ;
29.0(t) ; 31.6(t) ; 33.6(0 ; 34.1(0 ; 38.9(0 ; 32.1(d) ; 120.1(d); 125.7(d) ;
128.3(d) ; 128.3(d) ; 128.4(d) ; 128.4(d) ; 135.0(d); 142.54(s) ; 171.l(s)
8 ppm. MS : 308(0, M+); m/e, 198(1), 176(10), 158(66), 143(20), 127(95), 104(34),
91(56), 71(13), 57(100), 43(20).
i. methyl 3-acetoxy-2-pentyl-2-cvclopentene-1 -acetate
NMR('H, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 1.28(m, 5H) ; 1.41(m, 1H) ;
1.61(m, 1H) ; 1.79(m, 1H) ; 2.14(s, 3H) ; 2.03-2.26(m, 3H) , 2.46(m,
2H) ; 2.56(dd, Ji=4, J2=15, 1H) ; 3.04(m, 1H) ; 3.68(s, 3U) 8 ppm. NMR(13C, 90MHz, CDCI3) : 14.0(q) ; 20.7(q) ; 51.5(q) ; 22.4(0 ; 24.5(0 ;
26.8(0 ; 27.2(0 ; 29.6(0 ; 31.7(t) ; 38.6(0 ; 39.7(d) ; 128.3(s) ; 145.4(s) ;
168.5(s) ; 173.2(s) 5 ppm. MS : 268(1, M+); m/e, 226(10), 208(2), 195(3), 169(3), 153(100), 137(4), 123(3),
109(10), 97(35), 83(10), 67(9), 55(8), 43(31).
j. methyl 3-octanoyloxy-2-pentyl-l-cyclopentene-l-acetate
NMR(lH, 360MHz, CDCI3) : 0.88(t, J=7, 3H) ; 0.89(t, J=7, 3H) ; 1.30(m,
14H) ; 1.53-1.72(m, 3H) ; 1.79(m, 1H) ; 2.08(m, 1H) ; 2.19(m, 2H) ;
2.31-2.51 (m, 4H) ; 2.57(dd, ft =4, J2=15, 1H) ; 3.05(m, 1H) ; 3.68(s, 3H)
8 ppm. NMR(13C, 90MHz, CDCI3) : 14.0(q) ; 14.1 (q) ; 51.5(q) ; 22.4(0; 22.6(0;
24.5(0 ; 25.0(0 ; 26.8(0 ; 27.1(0 ; 28.9(0 ; 29.1(0 ; 29.6(0 ; 31.7(0 ;
31.7(0 ; 34.2(t); 38.6(0 ; 39.6(d) ; 128.2(s) ; 145.3(s) ; 171.5(s) ; 173.3(s)
6 ppm.
MS : 352(0, M+); m/e, 279(2), 226(92), 208(3), 194(4), 169(4), 153(100), 127(12), 109(7), 97(6), 81(5), 67(5), 57(22), 43(10).
Example 4
Test on fabrics
Several tests were caIRied out on fabrics, under a variety of conditions, said fabrics having been treated according to the following general method.
General method of treatment of textiles
A standard cotton swatch of 32 g was placed in a Linitest ® (origin : Manau, Germany) type vessel containing 1.3 g of a standard powder detergent base comprising 1% by weight of lipase (Lipolase ® 100T; origin : Novo Nordisk, Denmark) and 260 ml water. The cotton swatch was washed for 30 min at 40°. It was then taken out of the vessel and rinsed with 3x200 ml of water. It was then plunged for 5 min in 200 ml of water containing 0.6 g of a fabric softener base which contained a certain percentage by weight, comprised between 0.05 and 1%, of compound (I) according to the invention or, when applicable, of the coIResponding alcohol, aldehyde or ketone. The cotton swatch was then spin-dried without having been rinsed, and dried on a clothes line.
This method is equivalent to a washing in a real machine for washing 5 kg of linen in approximately 20 1 of water, with a rinsing of 4x20 1 water, the fabric softener being applied in the last rinsing water. The fabric softener base used had the following composition :
Ingredients % by weigth
Arquad 2 HT D (75%) 5.00
Formalin (40%) 0.20
Demineralized water 94.69
Colouring agent 2) 0.11
Total 100.00
1) origin : Akzo, Holland
2) Colanyl Blau AR/10% sol.; origin : Hoechst, Germany
In two separate tests, the cotton swatches were treated according to this general method, using as additive to the fabric softener respectively 9-decenyl hexadecanoate (1% by weight) in test A and 9-decenol (1% by weight) in test B.
The two swatches were submitted for a blind test evaluation 24 h after having been taken out of the Linitest ® apparatus. The evaluation panel consisted of eight people, to whom had been given beforehand a smelling strip which had been dipped in 9-decen-l-ol, so as to render them familiar with the odour of this compound. The panel was then asked to smell the two cotton swatches above-mentioned and to indicate if they could identify the odour of 9-decen-l-ol in either of the swatches. Five amongst the eight members of the panel recognized the odour of this alcohol in the swatch treated in test A and indicated that this odour was very powerful, whereas only one of said members was able to identify the odour on the swatch treated in test B.
A further evaluation of the two swatches caIRied" out by the same panel, under identical conditions, 24 h later, i.e. 48 h after taking the swatches out of the Linitest ® apparatus, showed that none of the panel members could identify the odour of 9-decen-l-ol on the swatch of test B, whereas six of said members identified it without any hesitation on the swatch coming out of test A.
Similar results were obtained when the two compounds above-mentioned were present in the fabric softener at a rate of 0.5% by weight.
Example 5
Test on fabrics
Nine standard cotton swatches (32 g each), numbered from 1 to 9, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener (at 1 % by weight) and described in Table 1 hereinafter.
TABLE 1
(Table Removed)

24 H after taking the swatches out of the Linitest ® machines, the nine cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having smelled 9-decen-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 2 hereafter (only categorical identifications were taken into account) :
TABLE 2
(Table Removed)
In a similar test caIRied out 48 h after having taken the swatches out of the Linitest ® machine, the members of the panel were still unanimous as regards swatch 1, i.e. they could not recognize the odour of 9-decen-l-ol on this swatch, whereas a majority judged it still very powerful on all the other swatches.
Example 6
Test on fabrics
Six standard cotton swatches (32 g each), numbered from 1 to 6, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener (at 1 % by weight) and described in Table 3 hereinafter.
TABLE 3
(Table Removed)
24 H after taking the swatches out of the Linitest ® machines, the six cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having smelled 9-decen-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 4 hereafter (only categorical identifications were taken into account) :
TABLE 4
(Table Removed)

The same test, caIRied out 48 h after having taken the swatches out of the Linitest ® machines, gave the results summarized in Table 5 hereinafter :
TABLE 5
(Table Removed)
Example 7 Test on fabrics
Six standard cotton swatches (32 g each), numbered from 1 to 6, were separately treated, and in identical manner, as described in Example 4. The detergent's content in lipase was now 3% by weight and the amount of fabric softener added to the last rinsing water was now 1.2 g. The additive incorporated (at 1% by weight) into the fabric softener in each case is cited in the following Table 6 :
TABLE 6
(Table Removed)
24 H after taking the swatches out of the Linitest ® machines, the six cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having smelled (E)-3,7-dimethyl-2,6-octadien-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 7 hereafter (only categorical identifications were taken into account) :
TABLE 7
(Table Removed)
Example 8 Test on fabrics
Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener and described in Table 8 hereinafter.
TABLE 8
(Table Removed)
24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of eleven individuals, whom, after having smelled (E)-3,7-dimethyl-6-octen-1-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on one or the other of the swatches- The result of this evaluation is summarized on Table 9 hereafter (only categorical identifications were taken into account) :
TABLE 9
(Table Removed)
A similar test caIRied out with two cotton swatches treated with the same fabric softener base but containing only 0.5% by weight of the compounds reported in Table 8. The panel evaluation showed that none of the panel members was able to identify the odour of the alcohol on swatch 1, whereas 7 of the 11 members of the panel were certain that they could smell it on swatch 2.
Still analogous results were obtained with a dosage of 0.1% by weight of the above-mentioned compounds.
Example 9 Test on fabrics
Three standard cotton swatches (32 g each), numbered from 1 to 3, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener (at 1% by weight) and described in Table 10 hereinafter.
TABLE 10
(Table Removed)
24 H after taking the swatches out of the Linitest ® machines, the three cotton swatches were submitted for a blind evaluation to a panel consisting of ten individuals, whom, after having srnelled 3-methyl-5-phenylpentan-l-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on any one of the swatches. The result of this evaluation is summarized on Table 11 hereafter (only categorical identifications were taken into account) :
TABLE 11
(Table Removed)
Example 10 Test on fabrics
Three standard cotton swatches (32 g each) were treated separately following the general method described in Example 4, two of said swatches (1 et 2) using 9-decen-l-ol as additive to the softener, and swatch 3 using as additive 9-decenyl hexadecanoate, these additives having been added to the fabric softener in a concentration of 0.5% by weight.
The three swatches were evaluated on a blind test by a panel of 12 individuals 24 h after having been taken out of the Linitest ® machines. The members of the panel were asked if they could ascertain any difference amongst the swatches and, if applicable, whether they could qualify this
difference. The panel had previously smelled strips dipped in 9-decen-l-ol and was aware that an evaluation of the three cotton swatches with regard to the particular odour of this compound was expected.
As a result of this evaluation, 8 out of the 12 members of the panel chose swatch 3 as being the one olfactively distinct and indicated that it developed the characteristic odour of 9-decen-l-ol, whilst the other two swatches gave off no distinctive odour.
The same test was caIRied out with 1% of additive in the softener, instead of 0.5%. In this case, 9 of the 12 members of the panel chose once again swatch 3 as being the one developing the odour of the above-mentioned alcohol, and indicated that this odour was even more powerful than in the preceding test. On the other hand, the panel found that the other two cotton swatches still exhaled no distinctive odour.
Example 11 Test on fabrics
Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated in the fabric softener, at a rate of 0.05% by weight, and described in Table 12 hereinafter.
TABLE 12
(Table Removed)

24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of twelve individuals, whom, after having smelled 3,7-dimethyl-2,6-octadien-1-ol on a smelling strip, had to indicate whether they recognized the odour of this alcohol on one or the other of the swatches. The result of this evaluation is summarized on Table 13 hereafter (only categorical identifications were taken into account) :
TABLE 13
(Table Removed)
Example 12
Test on fabrics
Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, but adding to the fabric softener 1% by weight of the additives cited in Table 14 hereinafter.
TABLE 14
(Table Removed)
24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of eleven individuals, whom, after having smelled 3,7-dimethyl-6-octenal on a smelling strip, had to indicate whether they recognized the odour of this aldehyde on one or the other of the swatches. The result of this evaluation is summarized on Table 15 hereafter (only categorical identifications were taken into account) :
TABLE 15
(Table Removed)
Example 13
Test on fabrics
Two standard cotton swatches (32 g each), numbered 1 and 2, were separately treated, and in identical manner, as described in Example 4, the only changing element being the additive incorporated (at 1% by weight) in the fabric softener and described in Table 16 hereinafter.
TABLE 16
(Table Removed)
24 H after taking the swatches out of the Linitest ® machines, the two cotton swatches were submitted for a blind evaluation to a panel consisting of twelve individuals, whom, after having smelled 3-methyl-5-phenyl-l-pentanal on a smelling strip, had to indicate whether they recognized the odour of this aldehyde on one or the other of the swatches. The result of this evaluation is summarized on Table 17 hereafter (only categorical identifications were taken into account) :
TABLE 17
(Table Removed)
Example 14
Test on fabrics
Three standard cotton swatches (32 g each) were treated separately following the general method described in Example 4, two of said swatches
(1 et 2) using 2-methyl-l-undecanal as additive to the softener, and swatch 3 using as additive 2-methyl-l-undecenyl octanoate, these additives having been added to the fabric softener in a concentration of 0.1% by weight. The three swatches were evaluated on a blind test by a panel of 12 individuals 24 h after having been taken out of the Linitest ® machines. The members of the panel were asked if they could ascertain any difference amongst the swatches and, if applicable, whether they could qualify this difference. The panel had previously smelled strips dipped in 2-methyl-l-undecanal and was aware that an evaluation of the three cotton swatches with regard to the particular odour of this compound was expected. As a result of this evaluation, 10 out of the 12 members of the panel chose swatch 3 as being the one olfactively distinct and indicated that it developed the characteristic odour of 2-methyl-l-undecanal, whereas the other two swatches gave off no distinctive odour.
Example 15 Test on fabrics treated in a washing machine
r
Two standard batches of cotton textiles, each comprising 30 cotton swatches (32 g each), were put into two separate washing machines, each containing, in the detergent compartment, 130 g of a standard powder detergent base comprising 1% by weight of lipase (Lipolase ® 100T; origin : Novo Nbrdisk, Denmark). In the compartment intended for the fabric softener, there was put, in one of the cases, 100 g of a softener base such as described in Example 4, perfumed with-0.1% by weight of 2-methyl-l-undecanal, whereas the softener (100 g) put in the second machine contained 0.1% by weight of 2-methyl-1-undecenyl octanoate. The batches of swatches were then washed with a normal washing cycle, at 40°, without prewash, and air dried. The batches of swatches were evaluated on a blind test, 24 h after having been taken out of the machines, by a panel of 36 individuals. The latter had to indicate if they found any difference at all amongst the three batches of swatches, of which two were identical and had been treated with the softener containing 2-methyl-l-undecanal (batches 1 and 2) and the third had been treated with 2-methyl-l-undecenyl octanoate (batch 3), without qualifying the nature of the distinctive character. In addition, they were
also asked to indicate whether any one of the batches possessed a more
powerful odour.
Of the 36 panellists, 24 identified textile batch 3 as being the one distinct
from the other two, from an olfactive point of view, and indicated that this
batch possessed a stronger odour than the other two.
An analogous test was caIRied out but with only two textile batches, batch A
having been treated with a softener containing 0.05% by weight of 2-
methyl-1-undecanal and batch B with a softener containing 0.05% by weight
of the coIResponding enol-ester, i.e. 2-methyl-l-undecenyl octanoate.
The panel of 36 individuals which evaluated batches A and B, without
knowing the nature of the perfuming ingredients, had to indicate which of
the two batches developed a stronger odour and which was prefeIRed from
the point of view of the perception of freshness and cleanliness of the
linen.
According to the categoric opinion of 32 out of the 36 panellists, the textiles
batch B was far more "perfumed" than batch A and was perceived as being
cleaner, with a more fresh odour.
Example 16 Tests on fabrics treated in a washing machine
A base perfuming composition was prepared by admixing the following ingredients :
(Table Removed)
1) trimethyI-13-oxabicyclo[10.1.0]trideca-4,8-diene; origin: Firmenich SA, Geneva, Switzerland
2) dodecahydro-3,6,6,9a-tetramethyl-naphto[2,l-b]furan ; origin : Firmenich SA, Geneva, Switzerland
3) tricyclo[5.2.1.02,6]dec~3-en-8-yl acetate; origin: Givaudan-Roure, Vernier, Switzerland
4) 2,6-dimethyl-7-octen-2-ol; origin : International Flavors & Fragrances, USA
5) l-(5,5-dimethyl-l-cyclohex-l-yl)-4-penten-l-one ; origin : Firmenich SA, Geneva, Switzerland
6) oxacyclohexadecan-2-one; origin : Firmenich SA, Geneva, Switzerland
7) origine : Firmenich SA, Geneva, Switzerland
8) methylionone; origin : Firmenich SA, Geneva, Switzerland
9) 3-(4-tert-butyl-l-phenyl)-2-methylpropanal; origin : Givaudan-Roure, Vernier, Switzerland
10) 4-(l,l-dimethylethyl)-cyclohexanol acetate ; origin : Firmenich SA, Geneva, Switzerland
11) cis-4-(l-methylethyl)-cyclohexanemethanol ; origin : Firmenich SA, Geneva, Switzerland
12) methyl ester of 3-oxo-l-pentyl~cyclopentaneacetic acid ; origin : Firmenich SA, Geneva, Switzerland
13) origin : Firmenich SA, Geneva, Switzerland
14) 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4~penten-2-ol; origin : Firmenich SA, Geneva, Switzerland
15) octahydro-5-methoxy-4,7-methano-lH-indene-2-carboxaldehyde; origin ; Firmenich SA, Geneva, Switzerland
16) 2,2,5-trimethyl-5-pentyl-cyclopentanone ; origin : Firmenich SA, Geneva, Switzerland
17) 2-tert-butyl-cyclohexanyl acetate; origin : International Flavors & Fragrances, USA
18) 2,4-dimethyl-3-cyclohexene-l-carbaldehyde ; origin : Firmenich SA, Geneva, Switzerland
Two perfuming compositions were prepared with this base composition, by adding thereto 150 parts by weight of geraniol or 3,7-dimethyl-2,6-octadienol (composition A), respectively 150 parts by weight of 3,7-dimethyl-2,6-octadienyl hexadecanoate (composition B).
These two perfuming compositions were then added, at the rate of 0.6% by weight, to a non-perfumed fabric softener base to prepare two samples, A and respectively B, of a perfumed softener.
In two identical washing machines, there were treated two standard batches of textiles, each formed of 1400 g of varied linen, comprising cotton swatches, cotton textiles and textiles in a cotton/polyester mixture. Each machine was charged with 130 g of a standard unperfumed detergent base containing 1% of lipase (Lipolase ® 100T). One of the machines was also charged with 100 g of sample A of the softener, comprising geraniol, whereas to the second machine there were added 100 g of softener sample B.
The linen was then washed at 40° in a normal washing cycle, without
prewash, and dried to air for 24 h.
Three standard batches of textiles, of which two were identical and had
been treated with sample A and the third with sample B, were then
evaluated on a blind test by a panel of 20 individuals, who had to identify
the batch of textiles possessing a distinct odour from that of the other two,
without qualifying the nature of the distinctive character. The panellists
also had to indicate which of the textile batches was more perfumed.
As a result of this test,, 14 panellists perceived a distinction in the odour of
the textile batch treated with the fabric softener sample B, while 10 out of
these 14 indicated that this same batch was the more perfumed.
When the evaluation was repeated after 48 h of drying to air, analogous
results were obtained.

We claim:
1. An ester of formula (I), as precursor of fragrant alcohol or ketone or
aldehyde
(Formula Removed)
wherein
a. R represents a radical derived from an fragrant alcohol of formula
ROH and Y represents a C7 to C24 linear or branched, saturated or
unsaturated alkyl radical, or a -(CH2)nCOOR group wherein R is defined
as above and n is an integer from 0 to 6; or
b. Y represents a C7 to C24 linear or branched, saturated or
unsaturated, alkyl radical and R represents a group of formula
(Formula Removed)
wherein, either R1 represents hydrogen and R2 represents an alkylidene radical derived from a fragrant aldehyde of formula
(Formula Removed)
or R2 represents an alkylidene radical and R1 an alkyl radical, R1 and R2 being then derived from an fragrant ketone of formula
(Formula Removed)
and, optionally, being part of a ring such as indicated by the dotted line which contains 5 to 18 carbon atoms and can be substituted.
2. A compound as claimed in claim 1, wherein R is the 9-decen-l-yl, 3,7-dimethyl-2,6-octadien- 1-yl, 3,7-dimethyl-6-octen-l -yl, 3-methyl-5-phenylpentyl, 3,7- dimethyl- 1,6-octadienyl, 3-methyl-5-phenyl-l-pentenyl or 2-methyl-l-undecenyl radical.
3. A compound as claimed in claim 1 or 2, wherein Y is a C12 to C24 linear alkyl radical.

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Patent Number

241595

Indian Patent Application Number

285/DEL/2003

PG Journal Number

29/2010

Publication Date

16-Jul-2010

Grant Date

14-Jul-2010

Date of Filing

12-Mar-2003

Name of Patentee

FIRMENICH SA,

Applicant Address

CASE POSTALE 239, 1, ROUTE DES JEUNES, 1211 GENEVA 8, SWITZERLAND,

Inventors:

#	Inventor's Name	Inventor's Address
1	WALTER PAGET	34 CHEMIN PRE-COLOMB, 1290 VERSOIX, SWITZERLAND,
2	DANIEL REICHLIN	235A RUE DE BERNEX 1232 CONFIGNON, SWITZERLAND
3	ROGER LESLIE SNOWDEN	"LA MAISON BLANCHE", LE FORT, 74580 VIRY, FRANCE
4	ERIC CHARLES WALBORSKY	886 BROWN ROAD, BRIDGEWATER, NEW JERSEY 08807, U.S.A
5	CHRISTIAN VIAL	5, RUE BAULACRE, 1202 GENEVA SWITZERLAND

PCT International Classification Number

C07C 067/00

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA