Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

A Synthesis of (Z)-Octadec-9-enedioic Acid

G Brunow, RV Stick, K Syrjanen, DMG Tilbrook and SJ Williams

Australian Journal of Chemistry 48(11) 1893 - 1897
Published: 1995


The monomethyl ester of azelaic acid was transformed into two fragments, namely [8-( methoxy -carbonyl) octyl ] triphenylphosphonium bromide and methyl 9-oxononanoate. A Wittig reaction between these two fragments produced dimethyl (Z)-octadec-9-enedioate and subsequent hydrolysis gave the title diacid. Interestingly, the same diacid was available directly from oleic acid in a published procedure which utilized a mutant strain of Candida tropicalis.

© CSIRO 1995

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