The Synthesis of Some Esters of Glycerol With Special Attention to the Problem of Acyl Migration

Abstract

Various triglycerides have been prepared by the acylation of either cis-1,3-O-benzylideneglycerol or 2,3-O-isopropylideneglycerol, followed by removal of the protecting group and acylation of the resultant diol. Alternatively, acylation of dihydroxyacetone, reduction of the intermediate ketone with sodium cyanoborohydride (pH 4) and acylation of the resultant alcohol also provide triglycerides in good yields. In some of these esters of glycerol, ¹³C n.m.r . spectroscopy (125.7 MHz) was used to monitor potential acyl migration. Finally, 2-halopyridinium salts were investigated as an alternative to the normal dicyclohexylcarbodiimide/dimethylaminopyridine couple for glycerol esterification.