The Reaction of lsopropyl β-Acetoxy-γ-methylthiobutyrate

Abstract

Previously, it was reported that isopropyl β-acetoxy-γ-methylthiobutyrate(2) and β-methylthio-γ-butyrolactone(3)were produced by refluxing isopropyl β-chloro-γ-methylthiobutyrate (1) in acetic acid. From kinetic studies, successive reaction path of (1)-(2)-(3) was expected.
However, competition reaction path was not ruled out. Therefore, the reaction of (2) was checked. The formation of (3) was recognized in the reaction of (2) in acetic acid. And, (3) and isopropyl aetate were formed with the heating of (2) in toluene in the presence of sulfuric acid. Probable reaction mechanism was proposed and some of the rate constant was evaluated.