The Synthesis of Diisobutylethylcarbinol

Abstract

Interest in the general problem of the synthesis of tie higher molecular weight, (C10 and higher ), tertiary alcohols was s timulated by the discovery that in a routine laboratory preparation involving the condensation of ethylmagnesium bromide and diisobutyl ketone the yield of the expected addition product was zero. This was a striking result in view of the fact that ethylmagnesium bromide and diisopropyl ketone give a 77 % yield of the addition product. A cursory search of the literature revealed that very little information was available concerning the syntnesis of the branched- chained tertiary alcohols. It was early recognized that to understand the results of the above attempted condensation, an extensive investigation of the action of Grignard reagents on branched ketones was necessary. The present problem, then, encompasses (1) the preparation and characterization of diisobutylethylcarbinol and (2) the study of the reaction of ethylmagnesium bromide with branched-chained ketones. [From Introduction]