Synthesis
General procedure for the synthesis of 3-chlorodiphenylmethanol from 3-chlorobenzophenone:
(1) To a mixed solution of ethanol (100 mL) and tetrahydrofuran (THF, 100 mL) of 3-chlorobenzophenone (10.0 g, 46.2 mmol), sodium borohydride (876 mg, 23.1 mmol) was slowly added at room temperature. The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was poured into water and extracted with ethyl acetate. The organic phases were combined, washed with water and then dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to give 3-chlorodiphenylmethanol as a colorless oil in a yield of 9.53 g (94.4% yield).
1H-NMR (CDCl3) δ: 2.55 (1H, d, J = 3.6 Hz), 5.80 (1H, d, J = 3.6 Hz), 7.25 to 7.40 (9H, m).
References
[1] Organic Letters, 2000, vol. 2, # 5, p. 659 - 661
[2] Patent: EP1437344, 2004, A1. Location in patent: Page 48
[3] Recueil des Travaux Chimiques des Pays-Bas, 1912, vol. 31, p. 311
[4] Recueil des Travaux Chimiques des Pays-Bas, 1915, vol. 34, p. 162
[5] Recueil des Travaux Chimiques des Pays-Bas, 1919, vol. 38, p. 121
