A. To a 400 ml methanol solution of 57 g (0.27 mol) of 3-trifluoromethyl-4-chlorobenzaldehyde was slowly added 9 g (0.24 mol) of sodium borohydride at 0°C to 10°C. The mixture was stirred for 3.5 h at room temperature and then filtered. The reaction mixture was stirred at room temperature for 3.5 hours and then filtered. The filtrate was concentrated under reduced pressure to give a solid residue which was dissolved in a mixture of 250 ml of water and 250 ml of chloroform. The aqueous phase was further extracted with 250 ml of chloroform. All chloroform extracts were combined and washed sequentially with 100 ml of 10% hydrochloric acid and 100 ml of water, followed by drying with anhydrous magnesium sulfate and filtration. The filtrate was concentrated under reduced pressure to give 49 g (86% yield) of brown-orange liquid, which crystallized on cooling and had a melting point of 26°C to 29°C.
