To a suspension of lithium aluminum hydride (11.6 g, 0.306 mol) in anhydrous tetrahydrofuran (350 mL) was added slowly and dropwise anhydrous tetrahydrofuran solution (50 mL) of trans-4-(trifluoromethyl)cyclohexanecarboxylic acid (30 g, 0.153 mol) at 0 °C. The reaction mixture was stirred continuously at 0°C for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent was petroleum ether:ethyl acetate = 10:1) to confirm complete consumption of raw materials. The reaction was quenched sequentially with water (12 mL), 15% aqueous sodium hydroxide solution (24 mL) and water (12 mL). The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give trans-(4-(trifluoromethyl)cyclohexyl)methanol (24 g, 86% yield) as a colorless liquid. The product was characterized by 1H NMR (CDCl3, 400 MHz): δ 3.49-3.50 (d, J = 6.0 Hz, 2H), 1.91-2.07 (m, 4H), 1.50-1.57 (m, 1H), 1.32-1.36 (m, 2H), 0.98-1.05 (m, 2H).
