Hydrochloric Acid → 4,4-Difluorocyclohexanecarboxylic acid

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A suspension of ethyl 4,4-difluorocyclohexanecarboxylate (2500 mg, 13 mmol) in ammonium hydroxide (28%, 50 ml) was stirred at 60° C. overnight. After removal of solvent, the residue was washed with water. The precipitate was obtained as product (white solid, 800 mg). 1H NMR (300 MHz, CDCl3): δ 5.31-5.45 (br, 2H), 2.02-2.27 (m, 3H), 1.92-2.02 (m, 2H), 1.72-1.87 (m, 4H). The mother liquor was acidified with 1N HCl to pH<1. The compound was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous sodium sulphate, filtered, condensed. 4,4-difluorocyclohexanecarboxylic acid was obtained as a 1200 mg of white solid which was further converted to 4,4-difluorocyclohexanecarboxamide by following procedure.

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