反应详情

To a well-stirred solution of 1,3-bis-(4-methoxybenzoyl)benzene 14 (1.80 g, 5.2 mmol) in dichloromethane (85 mL) was added boron trifluoride dimethyl sulfide complex (BF3.SMe2, 15 mL). The mixture was stirred for 27 h. After the reaction was quenched by water, the mixture was extracted with ethyl acetate (3×80 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under vacuum. The resulting solid was further purified using flash chromatography (silica gel, hexanes:ethyl acetate, 50:50) to afford the pure 1,3-bis-(4-hydroxybenzoyl)benzene 20 (0.62 g, 1.95 mmol) as a white solid in a 38% yield; 1H NMR (500 MHz, Acetone-d6): δ 9.28 (s, OH), 8.04 (td, J=1.7 Hz, 1.3 Hz, 1H, ArH), 7.98 (dd, J=7.7 Hz, 1.75 Hz, 2H, ArH), 7.80 (ddd, J=9.5 Hz, 4.8 Hz, 2.75 Hz, 4H, ArH), 7.73 (td, J=7.9 Hz, 0.45 Hz, 1H, ArH), 7.00 (ddd, J=9.5 Hz, 4.8 Hz, 2.75 Hz, 4H, ArH).

1. customAfter the reaction was quenched by water
2. extractionthe mixture was extracted with ethyl acetate (3×80 mL)
3. washThe combined organic layer was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under vacuum
6. customThe resulting solid was further purified