Aliphatic hydroxy-acids. Part III. Syntheses with alkyl 2-acetoxy-3-carboxypropionates
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 906-910
- https://doi.org/10.1039/j39680000906
Abstract
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.Keywords
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