Synthesis of 3,3,3-trifluoropropionic and 4,4,4-trifluoro-2-ketobutyric acids |
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Authors: | C Wakselman M Tordeux |
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Institution: | C.N.R.S.-C.E.R.C.O.A. 2, rue Henri Dunant 94320 Thiais France |
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Abstract: | Trifluoroethyl cyclohexyl ketone () is prepared by acylation of difluoroethylene () with cyclohexanecarboxylic acid chloride (), followed by Cl→F exchange with potassium fluoride in the presence of triethylbenzyl- ammonium chloride. Bayer-Villiger oxidation of ketone () with trifluoroperacetic acid gives cyclohexyl trifluoropropionate (). 3,3,3-trifluoropropionic acid () is obtained by treatment of () with trimethylsilyl iodide. Condensation of 2,2,2-trifluorodiazoethane () with ethyl glyoxylate () gives mainly ethyl 4,4,4-trifluoro-2-ketobutyric acid ester () which leads after hydrolysis to the corresponding acid (). |
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