Thionyl Chloride → 8-Acetyl-3-methoxy-benzo[c]chromen-6-one

Participants

Reaction Conditions

Reaction Steps

The compound from Step C was mixed with 1,2-dichloroethane (60 ml) and SOCl2 (1.7 ml, 23 mmol) was added. The mixture was refluxed for 90 min and then cooled to 0° C. AlCl3 (2.3 g, 17.3 mmol) was added and the reaction stirred at room temperature overnight. The solvent was removed and the crude product chromatographed on silica gel with hexane/ethyl acetate (1:1) to yield 5.1 g (90%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 2.74 (3H, s, COCH3), 3.94 (3H, s, OCH3), 6.92 (1H, s, ArH), 6.99 (1H, d, ArH), 8.02 (1H, d, ArH), 8.11 (1H, d, ArH), 8.41 (1H, d, ArH), 8.91 (1H, s, ArH).

Provenance & Evidence