General procedure for the synthesis of 3-chloro-1-phenylpropan-1-one from 3-chloropropiophenone: 3-chloro-1-phenylpropan-1-one (7.80 g, 46.26 mmol) was dissolved in a solvent mixture of THF (35 mL) and EtOH (35 mL) at -10 °C and protected by nitrogen with stirring. Sodium borohydride (2.20 g, 48.83 mmol) was added in batches over 10 min. The reaction mixture was continued to be stirred at -5 °C for 10 min, followed by slow pouring into a stirring mixture of saturated aqueous ammonium chloride solution (85 mL) and ice (40 g). The mixture was extracted twice with ether, the organic phases were combined, dried and the solvent was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate, gradient from 100/0 to 95/5) to give 3-chloro-1-phenylpropanol (7.50 g, 95% yield) as a pale yellow oil. Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) δ: 7.39 (d, 5H), 4.91-5.01 (m, 1H), 3.70-3.83 (m, 1H), 3.59 (s, 1H), 2.20-2.32 (m, 1H), 2.11 (d, 1H).
