Acetic Acid → 2',3'-Dihydroxyacetophenone

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 1,2-dihydroxybenzene (28)(2.0 g, 18.2 mmol) in AcOH (1.3 g, 21.7 mmol) was added boron trifluoride diethyl ether (98% in Et2O, 2 mL). The mixture was reacted under microwave irradiation (300 W) for 1.5 min and then cooled to 25° C. The reaction mixture was dissolved in dichoromethane (10 mL) and H2O (about 20 mL). The organic lay was washed with 10% NaHCO3 and then with water, dried over MgSO4 and concentrated. The crude was purified by column chromatography (SiO2, CH2Cl2) to give 30. Yellow solid; yield: 10.4%; mp 76-77° C.; 1H-NMR (CDCl3,200 MHz): δ 2.58 (s, 3H), 5.79 (s, 1H), 6.79 (t, J=8.0 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 12.45 (s, 1H); 13C-NMR (CDCl3, 50 MHz): δ 26.73, 118.79, 119.52, 120.39, 121.44, 145.40, 149.50, 205.08; Anal. calcd for C8H8O3: C, 63.15; H, 5.30. Found: C, 63.10; H, 5.33.

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