Sodium Iodide → 1-(3-Nitro-4-phenylmethoxyphenyl)ethanone

Participants

Reaction Steps

A mixture of 1-(4-hydroxy-3-nitrophenyl)ethanone (5.92 g, 32.70 mmol), sodium iodide (4.90 g, 32.70 mmol), potassium carbonate (13.55 g, 98.00 mmol), and benzyl bromide (5.04 mL, 42.50 mmol) in acetone (120 mL) was stirred under reflux for 66 h. After removal of solvent by rotary evaporation, the resulting residue was diluted with dichloromethane and insoluble inorganics were filtered off. The filtrate was concentrated in vacuo and the resulting residue was purified by flash silica gel column chromatography eluting with dichloromethane to give benzyl ether 2 as a white solid (8.24 g, 93%): 1H NMR (500 MHz, CDCl3) δ 2.60 (s, 3H), 5.32 (s, 2H), 7.18 (d, 1H), 7.41 (m, 5H), 8.12 (dd, 1H), 8.44 (d, 1H).

Provenance & Evidence