Mixed carboxylate sulphonate esters of glycerol

Abstract

Syntheses of the four mixed palmitate p-toluenesulphonate triesters of glycerol are described. Syntheses involving p-toluenesulphonic acid were in some cases accompanied by acyl migration. This was avoided by the use of p-toluenesulphonyl chloride in pyridine. The products were analysed by p.m.r. spectra in the presence of europium shift reagent. They underwent smooth reductive cleavage of p-toluenesulphonate on treatment with sodium borohydride.