Preparation of Benzyl γ-Benxoyloxybutyrates

Abstract

As part of our investigation of intramolecular phenolic coupling reactions we required a series of diesters of the general structure, 5 ¹. Since esters of γ-hydroxybutyric acid have been prepared by acid² or base³ catalyzed alcoholysis of γ-butyrolactone, it appeared that the desired esters might be prepared by alcoholysis of the lactone with a benzyloxide followed by trapping the new alkoxide, 1, with an acyl chloride. However, treatment of γ-butyrolactone with sodium benzyloxide under conditions analogous to those used in the preparation of ethyl γ-hydroxybutyrate³ failed to yield any of the corresponding benzyl ester. We were also unable to trap alkoxide 1 by acylation with acetyl chloride or benzoyl chloride.