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Improved preparation of 9-octadecenes

  • Martin E. Dyen
  • Herman C. Hamann
  • Daniel Swern
Technical

Abstract

cis- andtrans-9-Octadecenes have been obtained in about 55–60% yield on a preparative scale by an improved procedure from commercially pure oleyl alcohol (90–95%) and elaidyl alcohol, respectively, by conversion to the tosylates followed by reduction with lithium aluminum hydride (LAH). The improvement consists in using saturated sodium chloride solution to coagulate the slimy, intractable, insoluble salts obtained after the LAH reduction and destruction of excess LAH with water, prior to ether extraction of the crude hydrocarbons. Total time required for the preparation is about three days.

Keywords

Methyl Oleate Infrared Absorption Spectrum Oleyl Alcohol Lithium Aluminum Hydride Elaidate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

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    Elsner, B. B., and P. F. M. Paul, J. Chem. Soc.1953, 3156.Google Scholar
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    Nordby, H. E., B. W. Heywang, H. W. Kircher, A. R. Kemmerer, JAOCS39, 183 (1962).CrossRefGoogle Scholar
  3. 2.
    Swern, D., E. F. Jordan, and H. B. Knight, J. Am. Chem. Soc.68, 1673 (1946).CrossRefGoogle Scholar
  4. 3.
    Shreve, O. D., M. R. Heether, H. B. Knight and D. Swern, Anal. Chem.22, 1261 (1950).CrossRefGoogle Scholar

Copyright information

© The American Oil Chemists’ Society 1966

Authors and Affiliations

  • Martin E. Dyen
    • 1
  • Herman C. Hamann
    • 1
  • Daniel Swern
    • 1
  1. 1.Fels Research Institute and Department of ChemistryTemple UniversityPhiladelphia

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