消費者製品における感覚剤として有用なシクロヘキサン誘導体の合成

Japanese Patent JP5384641

B2

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-1) 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.

Kenneth, Edward, Jelm
Gregory, Mark, Banke
John, Christian, Hout

JP2011523155A

January 08, 2014

August 13, 2009

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THE PROCTER & GAMBLE COMPANY

C07C231/08; C07C51/08; C07C61/08; C07C67/08; C07C67/14; C07C69/75; C07C231/02; C07C231/06; C07C233/58; B01J27/122; C07B61/00

JP51012690B1
JP2007511546A
JP2007530689A
JP2004059474A
JP50093917A
JP2004536882A
JP2005068099A
JP2004107321A
JP2010513657A
JP9227455A

WO2004110972A1

Hirohito Katsunuma
Yukitaka Nakamura
Noritaka Yokota
Takeyasu Ito
Kazuma Kojima

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