Reduction of Long Chain and Bulky Carboxylic Esters by sodium tetrahydroborate

✍ Scribed by Prof. Dr. Angelo G. Giumanini; Dr. Franco Tubaro

• Book ID: 105353753
• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 479 KB
• Volume: 332
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19903320526

✦ Synopsis

Abstract

Methyl esters of long chain fatty acids as well as esters with functional (OH) and/or bulky substituents in alpha position and in the OR moiety may be effectively reduced with an excess of sodium tetrahydroborate at moderate temperature in dioxane‐water without catalysts. The reaction has been applied to the reduction of a pool of triglycerides of natural origin (virgin olive oil) in order to obtain a mixture of the acyl residues reduced to the corresponding alcohols without any structural or configurational modification. They, no matter which was the advancement of the reaction, seemed to reproduce quite well the overall acyl composition, as shown by GC‐MS analysis: the feasibility of such quantitative analysis may be extended, in order to obtain confirmatory evidences, on the component identifications and to perform specific separations, to the corresponding chlorides, hydrocarbons and trimethylsilylethers.