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Barbier-Wieland Degradation

Stepwise carboxylic acid degradation of aliphatic acids (particularly in sterol side chains) to the next lower homolog. The ester is converted to a tertiary alcohol that is dehydrated with acetic anhydride, and the olefin oxidized with chromic acid to a lower homologous carboxylic acid:

Barbier-Wieland Degradation

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