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

Participants

Reaction Steps

A mixture of 1-(4-hydroxy-3-nitrophenyl)ethanone (50.00 g, 276 mmol), sodium iodide (20.00 g, 133.4 mmol), potassium carbonate (115.00 g, 832.00 mmol), and benzyl bromide (43.00 mL, 362.00 mmol) in acetone (120 mL) was stirred under reflux for 16 h. The solids were removed by filtration and the filtrate concentrated by rotary evaporation. After this time the resulting residue was diluted with dichloromethane and insoluble inorganics were removed by filtration. The filtrate was concentrated in vacuo and the resulting residue was dissolved in hot chloroform. Hexanes were added to form a precipitate. The solids were collected by filtration to give benzyl ether 2 as a white solid (65.60 g, 87%): 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