Summary
The preparation of linolenaldehyde and of mixed aldehydes from highly unsaturated sources, such as menhaden oilvia the acyloin condensation, is described. Reduction of the acyloins and subsequent cleavage of the glycols gave over-all yields of 85 to 90% free aldehydes.
The intermediates in the synthesis as well as the final products were analyzed in part by the novel method of thin-layer silicic acid chromatography.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Mangold, H. K., J. Org. Chem.,24, 405 (1959).
Kaufmann, H. P., and Krischneck, H., Fette, Seifen, und Austrichmittel,60, 1125 (1958).
Bouquot, F., and Paquot, C., Bull. soc. chim. France, 440–441 (1949).
Gruger, E. H. Jr., Malins, D. C., and Gauglitz, E. J. Jr., J. Am. Oil Chemists’ Soc.,37, 214 (1960).
Mangold, H. K., and Malins, D. C., J. Am. Oil Chemists’ Soc., in press.
Malins, D. C., and Mangold, H. K., J. Am. Oil Chemists’ Soc., in press.
Stahl, E., Schröeter, G., Kraft, G., and Renz, R., Pharmazie,11, 633 (1956).
Hansley, V. L., J. Am. Chem. Soc.,57, 2303 (1935).
Kaufmann, H. P., and Krischneck, H., Fette, Seifen, und Anstrich mittel,55, 847 (1953).
Author information
Authors and Affiliations
Additional information
This is a laboratory of the Division of Industrial Research, U. S. Fish and Wildlife Service, Department of the Interior.
About this article
Cite this article
Gauglitz, E.J., Malins, D.C. The preparation of polyunsaturated aliphatic aldehydesvia the acyloin condensation. J Am Oil Chem Soc 37, 425–427 (1960). https://doi.org/10.1007/BF02631199
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02631199