LiAlH4 (2.0 M THF solution, 3.0 mL, 6.00 mmol) was dissolved in anhydrous THF (10 mL) under nitrogen protection and cooled to 0 °C. To this stirred mixture was added dropwise a solution of 4'-[4-(trifluoromethyl)phenyl]benzoic acid (0.4 g, 1.5 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at room temperature for 4 hours. Subsequently, H2O (0.23 mL), 3.0 M KOH solution (0.23 mL) and H2O (0.77 mL) were added slowly at 0 °C. The mixture was continued to be stirred at 0 °C for 1 h. The solid residue was removed by filtration and the organic phase was dried with Na2SO4. The organic solution was filtered again and concentrated to dryness. The crude product was purified by column chromatography using a Teledyne ISCO unit with the eluent cyclohexane/ethyl acetate (100:0 to 70:30) to afford 4'-trifluoromethyl-4-biphenylmethanol (0.3 g, 79%) as a white solid.1H NMR (DMSO-d6) data were as follows: δ 4.56 (d, J=5.7 Hz, 2H), δ 5.25 (t, J=5.7Hz, 1H), 7.45 (d, J=8.1Hz, 2H), 7.70 (d, J=8.1Hz, 2H), 7.81 (d, J=8.1Hz, 2H), 7.89 (d, J=8.1Hz, 2H).
