Convenient synthesis of 3,3,3-trifluoropropanoic acid by hydrolytic oxidation of 3,3,3-trifluoropropanal dimethyl acetal |
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| Authors: | Takeo Komata Shinya Akiba Katsuyuki Ogura |
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| Institution: | a Diversity and Fractal Science, Graduate School of Science and Technology, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi, Chiba 263-8522, Japan
b Chemical Research Center, Central Glass Co. Ltd., 2805 Imafuku-Nakadai, Kawagoe-shi, Saitama 350-1151, Japan |
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| Abstract: | A convenient and efficient method for preparing 3,3,3-trifluoropropanoic acid (1) is reported. The starting material is 1-chloro-3,3,3-trifluoropropene (2) that can be easily transformed into 3,3,3-trifluoropropanal dimethyl acetal (4) on treatment with methanol and KOH followed by acid-catalyzed addition of methanol. Direct transformation of 4 into 1 was efficiently achieved with 30% aqueous hydrogen peroxide (4.0 equiv.) in the presence of FeCl3 (0.025 equiv.) and hydrochloric acid (0.5 equiv.). |
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| Keywords: | 3 3 3-Trifluoropropanoic acid Acetal Hydrogen peroxide Hydrolytic oxidation |
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