Synthesis of long-chain Hydroxy Ketones from Hydroxy Acids

Abstract

The acyl chlorides derived from threo- and erythro-dihydroxystearic acid and -dihydroxybehenic acid, in which the alcohol groups are unreactive, are converted into ketene dimers by reaction with triethylamine and thence to long-chain tetra- hydroxy ketones. The ketones are apparently homogeneous but yet presumably consist of mixtures of stereoisomers. Certain other hydroxy acids in which the hydroxyl groups are more reactive may also be used to prepare ketones if they are first acetylated.