Derivatization of keto fatty acids: II. synthesis of long-chain enolacetates

Abstract

Long-chain enolacetates were prepared by refluxing the keto fatty acids with acetic anhydride and p-toluene sulfonic acid (p-TSA). 10-Oxoundecanoic and 2-oxohexadecanoic acids gave mainly 10-acetoxy-10-undecenoic and 2-acetoxy-2-hexadecenoic acids, respec-tively. On the other harld, 12-oxooctadecanoic acid on similar treatment was assumed to yield an isomeric mixture of 12-acetoxy-12(11)-octadecenoic acids. The structure of the individual reaction products were established by spectral studies. © 1983 American Oil Chemists.