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Journal of Lipid Research, Vol. 10, 631-635, November 1969
Copyright © 1969 by Lipid Research, Inc.

Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids

David R. Howton and Robert A. Stein

Laboratory of Nuclear Medicine and Radiation Biology, University of California, Los Angeles, California 90024, and Departments of Biophysics and Biological Chemistry, University of California at Los Angeles, School of Medicine, Los Angeles, California 90024

Three pentadecynoic acids, with the triple bond in the 8-, 9-, and 10-positions, have been synthesized on a gram scale in over-all yield of 65% by refinements of the five-step Ahmad-Strong method; isolation of intermediates was shown to be unnecessary prior to purification of the acetylenic nitriles by column chromatography on silicic acid.

The melting points of the pentadecynoic acids alternate regularly and widely with position of unsaturation, in marked contrast to behavior of the homologous octadecynoic acids described by Huber.

Supplementary key words acetylenic • carboxylic acids • nitriles • polymethylene halides • dimethyl sulfoxide • gas chromatography • silicic acid chromatography • primary alkyl iodide • UV spectrophotometry • acetylene ozonolysis • dioxocarboxylic acids

Submitted on October 14, 1968
Accepted on July 8, 1969

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