Acetone → 3,4-Bis-allyloxyxanthen-9-one

Participants

Reaction Steps

A stirred solution of 3,4-dihydroxyxanthen-9-one (290 mg, 1.27 mmol), allyl bromide (800 μL, 9.20 mmol), potassium carbonate hydrate (1.28 g, 7.77 mmol) and acetone (15.0 mL) was refluxed for 2.5 h. The solution was cooled to room temperature and dichloromethane was added. The mixture was filtered and the filtrate was rotary evaporated to yield 372 mg (95%) of the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.33 (dd, J1=7.84 Hz, J2=1.79, 1H), 8.07 (d, J=8.79 Hz, 1H), 7.72 (ddd, J1=8.10 Hz, J2=7.01, J3=1.65, 1H), 7.56 (dd, J1=8.51 Hz, J2=0.55, 1H), 7.38 (ddd, J1=7.76 Hz, J2=7.07, J3=1.03, 1H), 7.00 (d, J=9.06 Hz, 1H), 6.15 (m, 2H), 5.48 (m, 1H), 5.38 (m, 2H), 5.25 (m, 1H), 4.74 (m, 4H).

Provenance & Evidence