Sodium Hydroxide → 3,3-Difluoro-3-(4-fluorophenyl)propan-1-ol

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Reaction Steps

To a solution of acetic acid [3,3-difluoro-3-(4-fluorophenyl)-propyl]ester (5.50 g, 23.7 mmol) in ethanol (70 ml) is added 35% aqueous sodium hydroxide (20 ml) at 0° C. and the reaction mixture is stirred at RT for 1 h. After completion of reaction, the solvent is evaporated and the residue is diluted with water (150 ml) and acidified with aqueous hydrochloric acid before extraction with EtOAc (3×100 ml). The combined organic layers are washed with water (150 ml), brine (150 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield 3,3-difluoro-3-(4-fluorophenyl)-propan-1-ol (4.30 g, 22.6 mmol, 95%).

Provenance & Evidence