6-Methyl-5-hepten-2-one → 3,7-Nonadienoic acid, 4,8-dimethyl-, methyl ester

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Reaction Steps

6-Methyl-5-hepten-2-one is converted into 4,8-dimethylnona-3,7-dienoic acid by reaction with β-carboxyethyltriphenylphosphonium chloride in dimethylsulfoxide using the method of H. S. Corey et al., J. Am. Chem. Soc. 86, 1884 (1964). The trans and cis isomer can be separated by chromatography at this point or a mixture of the two isomers employed in further reactions. The acid is then converted into the acid chloride using thionyl chloride at roomm temperature or slightly higher. The acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes to yield the ester, methyl 4,8-dimethylnona-3,7-dienoate and ethyl 4,8-dimethylnona-3,7-dienoate.

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