Synthesis of triglycerides from 1,3-dibromopropan-2-ol

Abstract

1,3-Dibromopropan-2-ol (I) was converted into an acyl derivative (VI) by reaction with an appropriate acyl chloride in the presence of pyridine. The acyl derivative (VI) was subjected to nucleophilic substitution with 3 mol. equiv. tris(decyl)methylammonium carboxylate in refluxing hexane. This led to symmetrical diacid triglycerides in 90–94% yield. Substitution with an equimolar amount of the carboxylate afforded, predominantly, the 1,2-bisacyloxy-3-bromopropane (VII) which could be easily isolated and further substituted to give unsymmetrical diacid– and triacid–triglycerides in ca. 96% yield. Lipolysis showed the synthetic triglycerides to be ca. 99% pure.