Potassium Hydroxide → 4-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)benzoic acid

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Reaction Steps

A mixture of methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate (6.0 g, 24.2 mmol) and KOH (2.72 g, 48.4 mmol) in 1,4-dioxane (100 mL) and H2O (50 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature, evaporation of the solvent 1,4-dioxane in vacuo. The aqueous residue was acidified with 2N HCl and extracted with CH2Cl2. The extracts were washed with brine and dried. Flash chromatography of the residue, using 3:7 EtOAc-hexane, gave 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoic acid: 1H NMR (CDCl3) δ 11.0 (br, 1H), 7.95 (d, J=6.8 Hz, 2H), 7.71 (d, J=6.8 Hz, 2H), 6.73 (s, 1H), 1.71 (s, 3H); ms 235.0 (M+H+).

Provenance & Evidence