Conversion of methyl ricinoleate to methyl 12-ketostearate with Raney nickel

Autor: Freedman, Bernard, Nelson, Jane S., Binder, R. G., Applewhite, T. H.
Zdroj: Journal of the American Oil Chemists' Society; April 1965, Vol. 42 Issue: 4 p340-344, 5p
Abstrakt: A convenient laboratory preparation of methyl 12-ketostearate is described. Methyl ricinoleate is converted to methyl 12-ketostearate in 70?75% yield by Raney nickel. The type and quantity of Raney nickel have a marked influence on the yield as well as on the time and temp required for the conversion. The reaction is not a direct isomerization as previously assumed but appears to be a two-step process. Methyl ricinoleate is hydrogenated rapidly to methyl 12-hydroxystearate which is then dehydrogenated slowly to the product. Hydrogenolysis of the alcohol function is a competing reaction which is minimized by the proper choice of reaction conditions.
Databáze: Supplemental Index