Diethyl butylmalonate → Phytanic Acid

Participants

Reaction Steps

The 2-benzylalkanoic and 2-butylalkanoic acids were prepared by the malonic ester method starting from diethyl benzylmalonate or diethyl butylmalonate and the appropriate alkyl bromide. The procedure used was analogous to that for the preparation of 2-methyldecanoic acid. Preparation of 2,2-dibutyldodecanoic acid was accomplished by alkylation of 2-butyldodecanoic acid using the method of Pfeffer, Silbert, and Chirinko. Hydrogenation of phytol followed by oxidation of the resulting saturated alcohol with a solution of chromium trioxide in acetic acid gave 3,7,11,15-tetramethylhexadecanoic acid.

Provenance & Evidence