General procedure for the synthesis of 5H-dibenzo[a,d]cyclohepten-5-ol from 5-dibenzo[a,d]cycloheptenone: 1.50 g (7.27 mmol) of 5-dibenzo[a,d]cycloheptenone was added to a suspension containing 4 mL of water, 0.45 mL of 1N aqueous sodium hydroxide solution and 20 mL of methanol, followed by 200 mg (5.29 mmol) of sodium borohydride. The reaction mixture was stirred overnight. Upon completion of the reaction, the precipitated crystals were collected by filtration, washed with water, and then the crystals were dissolved in ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and the solvent was subsequently evaporated under reduced pressure to give 5H-dibenzo[a,d]cyclohepten-5-ol. Yield: 1.48 g (7.11 mmol) in 98% yield.1H-NMR (CDCl3) data: δ 2.41 (1H, d), 5.43 (1H, d), 7.11 (2H, s), 7.25-7.31 (2H, m), 7.36-7.44 (4H, m), 7.66 (2H, d).
