Reaction Steps
To a well-stirred solution of 1,3-bis-(4-methoxybenzoyl)benzene 14 (700 mg, 2.02 mmol) in dichloromethane (25 mL) was added boron trifluoride dimethyl sulfide complex (BF3.SMe2, 10 mL). The reaction was stirred for 16 h at room temperature, and then quenched with water, and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified using flash chromatography (silica gel, hexanes:ethyl acetate, 50:50) to afford the pure 1-(4-hydroxybenzoyl)-3-(4-methoxybenzoyl)benzene 16 (0.2 g, 0.60 mmol) as a white solid in a 30% yield; 1H NMR (500 MHz, Acetone-d6): δ 9.19 (s, OH), 7.89 (dt, J=2 Hz, 0.5 Hz, 1H, ArH), 7.85 (dd, J=7.5 Hz, 1.5 Hz, 2H, ArH), 7.72 (ddd, J=10.0 Hz, 5.0 Hz, 3.0 Hz, 2H, ArH), 7.66 (ddd, J=9.5 Hz, 5.0 Hz, 3.0 Hz, 2H, ArH), 7.59 (td, J=7.5 Hz, 0.5 Hz, 1H, ArH), 6.96 (ddd, J=9.5 Hz, 4.5 Hz, 2.5 Hz, 2H, ArH), 6.86 (ddd, J=9.5 Hz, 5.0 Hz, 3.0 Hz, 2H, ArH), 3.78 (s, 3H, OCH3); 13C NMR (125 MHz, Acetone-d6): δ 193.70, 193.56, 163.61, 161.941, 138.58, 138.35, 132.62, 132.41, 132.30, 130.16, 129.67, 128.75, 128.56, 115.25, 113.78, 55.12.
