Journal of Lipid Research, Vol. 13, 23-26, January 1972
Copyright © 1972 by Lipid Research, Inc.

Reductive and oxidative synthesis of saturated and unsaturated fatty aldehydes

William J. Ferrell and Kuo-Ching Yao

Department of Chemistry, University of Detroit, Detroit, Michigan 48221

Saturated and unsaturated fatty aldehydes were synthesized 99+% pure with yields of up to 80% by the reduction of 1-acylaziridines with lithium aluminium hydride, and in yields of up to 87% by oxidation of the corresponding alcohol with 1-chlorobenzotriazole. It was found for the reduction that optimum aldehyde yield was obtained with a mole ratio of reactants, consisting of acid chloride-ethylenimine-triethylamine-LiAlH₄, equal to 1:2:2:2. Optimum conditions for alcohol oxidation were found to be a mole ratio of oxidant to alcohol of 1:1.3 with refluxing for 45 min in methylene chloride containing 25% pyridine. Methods for the purification of the final product are also described. Purity criteria were thin-layer and gas-liquid chromatography and infrared and nuclear magnetic resonance spectroscopy.

Supplementary key words fatty alcohol • lithium aluminum hydride • 1-acylaziridines • thin-layer chromatography • gas-liquid chromatography • 1-chlorobenzotriazole

Submitted on March 26, 1971
Accepted on July 22, 1971

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