Abstract
2, 15-Hexadecanedione (5), a key intermediate for the synthesis of dl-muscone, was prepared from alkyl sulfone. The Claisen condensation of 1, 6-bis (p-toluenesulfonyl) hexane (1) and ethyl 4, 4- (ethylenedioxy) valerate afforded 2, 2, 15, 15-bis (ethylenedioxy) -6, 11-bis (p-toluenesulfonyl) -5, 12-hexadecanedione (2) in quantitative yield. The reductive elimination of the sulfonyl groups, the Wolff-Kishner reduction, and hydrolysis of the diacetal gave 2, 15-hexadecanedione (5) in good yield.
