Abstract: After the lactone portion of trans-whiskey lactone is hydrolyzed with potassium hydroxide, this portion is reacted with isopropyl bromide and mixed with an alkyl group, thereby obtaining isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate. Then, the isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate is reacted with diethyl azodicarboxylate in the presence of triphenylphosphine and azodicarboxylate, thereby obtaining isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate. The isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate is hydrolyzed in 2% potassium hydroxide, and as a result, cis-whiskey lactone (A) represented by the following general formula is obtained. According to this method, cis-whiskey lactone, one of the perfume components of whiskey and wine, can be produced selectively and easily.
Type:
Grant
Filed:
August 27, 1992
Date of Patent:
November 21, 1995
Assignees:
Japan Tobacco Inc., Yuji Gosei Kogyo Co., Ltd.