Abstract
Methyl 9(10)-formylstearate was converted to methyl 9(10)-carboxymethylstearate. The reactions to prepare the intermediates methyl 9(10)-hydroxymethyl-, 9(10)-ace toxymethyl-, 9(10)-methylene-, and 9(10)-formylmethylstearate are described. Methyl 9(10)-hydroxy methylstearate readily loses methanol and forms a trimeric polymer. The acetate of the primary alcohol when pyrolyzed gives 59% yield of methyl 9(10)-methylenestearate. Hydroformylation of the methylene compound followed by permanganate oxidation gave methyl carboxymethylstearate. Evidence is presented to show that pyrolysis of the acetate ester and hydroformylation of the pyrolysis product produce, respectively, only the methylene and formylmethylstearates. Rates of esterification-transes terification of methyl 9(10)-carboxymethyl sterate show that the carboxymethyl group is 2–3 times as active as the carboxyl group in methyl 9(10)-carboxystearate and that the terminal carboxyl group is about 10 times more active towards esterification than the branched carboxymethyl group.
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Dufek, E.J. Conversion of methyl 9(10)-formylstearate to carboxymethylstearate. J Am Oil Chem Soc 55, 337–339 (1978). https://doi.org/10.1007/BF02669924
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DOI: https://doi.org/10.1007/BF02669924