YELM, KENNETH EDWARD,BUNKE, GREGORY MARK,HAUGHT, JOHN CHRISTIAN
申请号：
CA2731967
公开号：
CA2731967C
申请日:
2009.08.13
申请国别(地区):
CA
年份:
2014
代理人:
摘要：
The present invention provides synthetic routes for preparing various isomersof cyclohexane-based coolants, suchas menthyl esters and menthanecarboxamide derivatives, in particular thosesubstituted at the amide nitrogen, for example with anaromatic ring or aryl moiety. Such structures have high cooling potency andlong lasting sensory effect, which make them usefulin a wide variety of consumer products. One synthetic route involves a coppercatalyzed coupling of a primary menthanecarboxamidewith an aryl halide, such reaction working best in the presence of potassiumphosphate and water. Using this syntheticroute, specific isomers can be prepared including the menthanecarboxamideisomer having the same configuration as l-mentholand new isomers such as a neoisomer having opposite stereochemistry at thecarboxamide (C-1) position. The neoisomer unexpectedlyhas potent and long lasting cooling effect. Preparation schemes for neoisomersof other menthyl derivatives which areuseful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.
