Aliphatic hydroxy-acids. Part III. Syntheses with alkyl 2-acetoxy-3-carboxypropionates

Methyl (±)-2-acetoxy-3-carboxypropionate has been prepared from (±)-malic acid and used in crossed Kolbe electrolyses to prepare dimethyl (±)-2-acetoxydodecane-1,12-dioate and three methyl 2-acetoxyalkanoates. Dimethyl and diethyl meso-2,5-diacetoxyadipates have been isolated from the Kolbe electrolyses of methyl and ethyl (±)-2-acetoxy-3-carboxypropionates respectively, and the presence of the corresponding (±)-2,5-diacetoxyadipates has been established. Lithium aluminium hydride reduction of diethyl meso-2,5-diacetoxyadipate gives meso-hexane-1,2,5,6-tetraol.