Title of Invention	"PROCESS OF PREPARATION OF 2-METHYL-4(2,2,3-TRIMETHYL CYCLOPENT-3-EN-1-YL) BUT-2-EN-OL (AS FINE SANDAL CORE)"
Abstract	A process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol Comprising the steps of reacting pinene epoxide with toluene and/or di-butylphthalate at a temperature of 100-120 deg c in presence of zinc bromide as catalyst to form alpha-campholenic aldehyde, reacting alpha-campholenic aldehyde with propane aldehyde in presence of methanol and sodium methoxide as catalyst at a temperature of 60-65 deg c to get a mass, subjecting the above mass to vaccum distillation to get a distilled mass, reducing the above distilled mass in presence of methanol and sodium borohydride, subjecting the reduced mass to vaccume distillation to get the compound of formula I having 95% purity, wherein towards the end of distillation temperature is raised to 160 degc.

Title of Invention

"PROCESS OF PREPARATION OF 2-METHYL-4(2,2,3-TRIMETHYL CYCLOPENT-3-EN-1-YL) BUT-2-EN-OL (AS FINE SANDAL CORE)"

Abstract

A process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol Comprising the steps of reacting pinene epoxide with toluene and/or di-butylphthalate at a temperature of 100-120 deg c in presence of zinc bromide as catalyst to form alpha-campholenic aldehyde, reacting alpha-campholenic aldehyde with propane aldehyde in presence of methanol and sodium methoxide as catalyst at a temperature of 60-65 deg c to get a mass, subjecting the above mass to vaccum distillation to get a distilled mass, reducing the above distilled mass in presence of methanol and sodium borohydride, subjecting the reduced mass to vaccume distillation to get the compound of formula I having 95% purity, wherein towards the end of distillation temperature is raised to 160 degc.

Full Text	Field of Invention The present invention relates to a process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol which can be used as sandal powder. The present compound has a powerful sandalwood odour of excellent diffusivity. The molecular formula of the compound is C13H22O having a molecular weight of 194.32 having the structure of formula I. The compound is colourless to pale yellow in appearance and is a slightly viscous liquid. The density of the compound at 25 deg c is 0.9180 to 0.9320 and flash point is more than 100 deg c. The recovery of the compound is approx 95% which is sum of all its isomers. (Formula Removed) Formula I Wherein Rl, R2, R3 and R4 are sum of isomers. Background of the Invention Applicants know no prior art relating to the process of preparation of the compound of formula I. The present process is novel, inventive and industrially applicable. Statement of the Invention Accordingly, a process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol of the formula I Wherein R1, R2, R3 and R4 are sum of isomers. Comprising the steps of (a) reacting pinene epoxide with toluene and/or di-butylphthalate at a temperature of 100-120 deg c in presence of zinc bromide as catalyst to form alpha-campholenic aldehyde, (b) reacting alpha-campholenic aldehyde with propane aldehyde in presence of methanol and sodium methoxide as catalyst at atemperature of 60-65 deg c to get amass, (c) subjecting the above mass to vaccum distillation to get a distilled mass, (d) reducing the above distilled mass in presence of methanol and sodium borohydride, (e) subjecting the reduced mass to vaccume distillation to get the compound of formula I, wherein towards the end of distillation temperature is raised to 160 deg c. A preferred embodiment is wherein the vaccume distillation is carried out at 730-755 mm/Hg. Another embodiment is wherein the reduction reaction is carried out at a temperature range of 8-12 deg c. A further embodiment is wherein the product yield is 65-75%. Detailed description of the invention The following are the details of the process for the preparation of the compound of formula I. 1.1 Pinene epoxide and toluene is reacted at a temperature range of 100 c-110 c in presence of zinc bromide as catalyst and alpha-campholenic aldehyde is formed. This is a batch process. During the reaction some impurities are generated which are fractionated in the column under vacuum. 1.2 Pinene epoxide is passed through di-butylphthalate under vaccum of 735-745mm/Hg at temperature range of 110 c -120 c in presence of zinc bromide as catalyst. This is a continuous process. Alpha-campholenic aldehyde (80-85%), low boilers (6-9%) and high boilers (5-8%) are formed. This mass is fractionated in the column under vaccum to get a product yield of alpha-compholenic aldehyde (75-80%), recycles (10-15%) and residues (12-15%). The alpha-campholenic aldehyde produced is of 85% purity. 1.3 Alpha-campholenic aldehyde and propane aldehyde is reacted at a temperature range of 60-65 c in presence of methanol and sodium methoxide as catalyst. The product formed is called Fine Sandal core. During the reaction some impurities are framed along with unconverted alpha-campholenic aldehyde and propane aldehyde. This mass is washed with water and distilled. The product of following purity are formed — Fine Sandal core - 65% Dimer-15% Alpha-campholenic aldehyde -10% High boiler-5% Low boiler - 5% 1.4 The crude of the above step is distilled at a temperature range of 135-160 c under vaccume of 730-755mm/Hg. The top fraction is the impurities and is removed. The middle fraction is collected. The bottom fraction is removed as residue. The product yield is as follows - Fine Sandal core - 75-85% Recycles-15-20% Low boiler-25-30% Residue-15-20% The purity is as follows -Middle fraction mass - 95% Low boiler-2% High boiler -3% 1.5 The distilled Fine Sandal core is reduced hi presence of methanol and sodium borohydride at a temperature range of 8-12 c. During the reaction some impurities are formed which are washed with water. The washed crude is distilled under vaccum. The product purity after reduction is as follows - Fine Sandal core - 92% Low boiler - 5% High boiler -3% 1.6 The above obtained reduced mass is distilled under vaccume. When the end of distillation approaches, the temperature is raised to 160 c. The top fraction is collected as low boiler, middle fraction is collected as product and the bottom mass is drained out as residue. The yield is as follows — Fine sandal core - 65-75% Recycles-15-18% Residue-10-12% The purity is as follows - Fine sandal core (Sum of all isomers) - 95% Low boilers - 2% High boilers - 3% We claim- 1. A process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol of the formula I (Formula Removed)Wherein Rl, R2, R3 and R4 are sum of isomers. Comprising the steps of- (f) reacting pinene epoxide with toluene and/or di-butylphthalate at a temperature of 100-120 deg c in presence of zinc bromide as catalyst to form alpha-campholenic aldehyde, (g) reacting alpha-campholenic aldehyde with propane aldehyde in presence of methanol and sodium methoxide as catalyst at a temperature of 60-65 deg c to get amass, (h) subjecting the above mass to vaccum distillation to get a distilled mass, (i) reducing the above distilled mass in presence of methanol and sodium borohydride, (j) subjecting the reduced mass to vaccume distillation to get the compound of formula I having 95% purity, wherein towards the end of distillation temperature is raised to 160 deg c. 2. A process as claimed in claim 1, wherein the vaccume distillation is carried out at 730-755 mm/Hg. 3 A process as claimed in claim 1, wherein the reduction reaction is carried out at a temperature range of 8-12 deg c. 4. A process as claimed in claim 1, wherein the product yield is 65-75%. 5. A process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2- en-ol of the formula I substantially as herein described.

Full Text

Field of Invention
The present invention relates to a process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol which can be used as sandal powder. The present compound has a powerful sandalwood odour of excellent diffusivity. The molecular formula of the compound is C13H22O having a molecular weight of 194.32 having the structure of formula I. The compound is colourless to pale yellow in appearance and is a slightly viscous liquid. The density of the compound at 25 deg c is 0.9180 to 0.9320 and flash point is more than 100 deg c. The recovery of the compound is approx 95% which is sum of all its isomers.
(Formula Removed)
Formula I
Wherein Rl, R2, R3 and R4 are sum of isomers.
Background of the Invention
Applicants know no prior art relating to the process of preparation of the compound of formula I. The present process is novel, inventive and industrially applicable.
Statement of the Invention
Accordingly, a process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol of the formula I
Wherein R1, R2, R3 and R4 are sum of isomers. Comprising the steps of
(a) reacting pinene epoxide with toluene and/or di-butylphthalate at a temperature of
100-120 deg c in presence of zinc bromide as catalyst to form alpha-campholenic
aldehyde,
(b) reacting alpha-campholenic aldehyde with propane aldehyde in presence of
methanol and sodium methoxide as catalyst at atemperature of 60-65 deg c to get
amass,
(c) subjecting the above mass to vaccum distillation to get a distilled mass,

(d) reducing the above distilled mass in presence of methanol and sodium
borohydride,
(e) subjecting the reduced mass to vaccume distillation to get the compound of
formula I, wherein towards the end of distillation temperature is raised to 160 deg
c.
A preferred embodiment is wherein the vaccume distillation is carried out at 730-755 mm/Hg.
Another embodiment is wherein the reduction reaction is carried out at a temperature range of 8-12 deg c.
A further embodiment is wherein the product yield is 65-75%. Detailed description of the invention
The following are the details of the process for the preparation of the compound of formula I.
1.1 Pinene epoxide and toluene is reacted at a temperature range of 100 c-110 c in
presence of zinc bromide as catalyst and alpha-campholenic aldehyde is formed. This is a
batch process. During the reaction some impurities are generated which are fractionated
in the column under vacuum.
1.2 Pinene epoxide is passed through di-butylphthalate under vaccum of 735-745mm/Hg
at temperature range of 110 c -120 c in presence of zinc bromide as catalyst. This is a
continuous process. Alpha-campholenic aldehyde (80-85%), low boilers (6-9%) and high
boilers (5-8%) are formed. This mass is fractionated in the column under vaccum to get a
product yield of alpha-compholenic aldehyde (75-80%), recycles (10-15%) and residues
(12-15%). The alpha-campholenic aldehyde produced is of 85% purity.
1.3 Alpha-campholenic aldehyde and propane aldehyde is reacted at a temperature range
of 60-65 c in presence of methanol and sodium methoxide as catalyst. The product
formed is called Fine Sandal core. During the reaction some impurities are framed along
with unconverted alpha-campholenic aldehyde and propane aldehyde. This mass is
washed with water and distilled. The product of following purity are formed —
Fine Sandal core - 65%
Dimer-15%
Alpha-campholenic aldehyde -10%
High boiler-5%
Low boiler - 5%
1.4 The crude of the above step is distilled at a temperature range of 135-160 c under
vaccume of 730-755mm/Hg. The top fraction is the impurities and is removed. The
middle fraction is collected. The bottom fraction is removed as residue. The product yield
is as follows -
Fine Sandal core - 75-85% Recycles-15-20% Low boiler-25-30% Residue-15-20%
The purity is as follows -Middle fraction mass - 95% Low boiler-2% High boiler -3%
1.5 The distilled Fine Sandal core is reduced hi presence of methanol and sodium
borohydride at a temperature range of 8-12 c. During the reaction some impurities are
formed which are washed with water. The washed crude is distilled under vaccum. The
product purity after reduction is as follows -
Fine Sandal core - 92% Low boiler - 5% High boiler -3%
1.6 The above obtained reduced mass is distilled under vaccume. When the end of
distillation approaches, the temperature is raised to 160 c. The top fraction is collected as
low boiler, middle fraction is collected as product and the bottom mass is drained out as
residue. The yield is as follows —
Fine sandal core - 65-75%
Recycles-15-18%
Residue-10-12%
The purity is as follows -
Fine sandal core (Sum of all isomers) - 95%
Low boilers - 2%
High boilers - 3%

We claim-
1. A process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-en-ol of the formula I
(Formula Removed)Wherein Rl, R2, R3 and R4 are sum of isomers. Comprising the steps of-
(f) reacting pinene epoxide with toluene and/or di-butylphthalate at a temperature of
100-120 deg c in presence of zinc bromide as catalyst to form alpha-campholenic
aldehyde,
(g) reacting alpha-campholenic aldehyde with propane aldehyde in presence of
methanol and sodium methoxide as catalyst at a temperature of 60-65 deg c to get
amass,
(h) subjecting the above mass to vaccum distillation to get a distilled mass,
(i) reducing the above distilled mass in presence of methanol and sodium
borohydride, (j) subjecting the reduced mass to vaccume distillation to get the compound of
formula I having 95% purity, wherein towards the end of distillation temperature
is raised to 160 deg c.
2. A process as claimed in claim 1, wherein the vaccume distillation is carried out at 730-755 mm/Hg.
3 A process as claimed in claim 1, wherein the reduction reaction is carried out at a temperature range of 8-12 deg c.
4. A process as claimed in claim 1, wherein the product yield is 65-75%.
5. A process of preparation of 2-Methyl-4(2,2,3-Trimethyl Cyclopent-3-en-l-yl) but-2-
en-ol of the formula I substantially as herein described.

Documents:

28-del-2005-abstract.pdf

28-DEL-2005-Claims.pdf

28-del-2005-correspondence-others.pdf

28-del-2005-correspondence-po.pdf

28-del-2005-description (complete).pdf

28-del-2005-description (provisional).pdf

28-del-2005-form-1.pdf

28-del-2005-form-18.pdf

28-del-2005-form-2.pdf

28-del-2005-form-3.pdf

28-del-2005-form-5.pdf

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Patent Number

226228

Indian Patent Application Number

28/DEL/2005

PG Journal Number

01/2009

Publication Date

02-Jan-2009

Grant Date

12-Dec-2008

Date of Filing

06-Jan-2005

Name of Patentee

FINE ORGANICS

Applicant Address

C/7-10, ROSHANBAGH INDUSTRIAL ESTATE, RAMPUR, U.P.-244901, INDIA.

Inventors:

#	Inventor's Name	Inventor's Address
1	GUPTA NEERAJ	B-8, ROSHANBAGH INDUSTRIAL ESTATE, RAMPUR-244901 U.P.-INDIA.

PCT International Classification Number

B01D 3/00

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA