Journal of the Chemical Society. Perkin transactions II p. 1553 - 1558 (1983)
Update date:2022-08-04
Topics:
Bhati, Asharam
Hamilton, Richard J.
Steven, David A.
Aneja, Rajender
Padley, Frederick B.
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 90-94percent 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. 96percent yield.Lipolysis showed the synthetic triglycerides to be ca. 99percent pure.
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