Title of Invention	"SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS"
Abstract	The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-l) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

Title of Invention

"SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS"

Abstract

The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-l) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

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Patent Number

272182

Indian Patent Application Number

718/DELNP/2011

PG Journal Number

13/2016

Publication Date

25-Mar-2016

Grant Date

21-Mar-2016

Date of Filing

31-Jan-2011

Name of Patentee

THE PROCTER & GAMBLE COMPANY

Applicant Address

ONE PROCTER & GAMBLE PLAZA, CINCINNATI, OH 45202, UNITED STATES OF AMERICA

Inventors:

#	Inventor's Name	Inventor's Address
1	YELM, KENNETH, EDWARD	6231 CROSSCREEK COURT, HAMILTON, OH 45011, UNITED STATES OF AMERICA
2	BUNKE, GREGORY, MARK	23947 GABBARD DRIVE, LAWRENCEBURG, IN 47025, UNITED STATES OF AMERICA
3	HAUGHT, JOHN, CHRISTIAN	8420 TWIN COVE COURT, WEST CHESTER, OH 45069, UNITED STATES OF AMERICA

PCT International Classification Number

C07C 231/08

PCT International Application Number

PCT/US2009/053634

PCT International Filing date

2009-08-13

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	61/089,094	2008-08-15	U.S.A.