Abstract
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.
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A laboratory of the W. Utiliz. Res. & Dev. Div., ARS, USDA.
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Freedman, B., Nelson, J.S., Binder, R.G. et al. Conversion of methyl ricinoleate to methyl 12-ketostearate with Raney nickel. J Am Oil Chem Soc 42, 340–344 (1965). https://doi.org/10.1007/BF02540143
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DOI: https://doi.org/10.1007/BF02540143