Stobbe-type condensation involving diethyl diglycollate

Abstract

Benzaldehyde, p-anisaldehyde, acetophenone and acetone condense with diethyl diglycollate in the presence of sodium hydride to give fairly good yields of the corresponding half-esters. With benzaldehydeand p-anisaldehyde the (Z)-half-esters (2a) and (2b) predominated. Condensation with benzophenone was only effected with potassium t-butoxide in boiling t-butyl alcohol. The structure and configuration of the half-esters was established by chemical and spectroscopic evidence.