General synthetic routes to β-hydroxy-acids from t-butyl esters and the Reformatskii reaction

Abstract

A wide range of β-hydroxy-acids are synthesised in high yields by (a) the dealkylation of t-butyl β-hydroxy-esters, prepared by the Reformatskii reaction, and (b) a modified Reformatskii procedure which leads directly to the hydroxy-acid. With highly hindered ketones or under conditions of inverse addition, self-condensation of the Reformatskii reagents from the t-butyl esters of α-bromopropionic acid and α-bromoisobutyric acid seriously reduce the yields of β-hydroxy-esters.