Acetone → 1-(allyloxy)-2-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-nitrophenol (5.2 g, 0.037 mol) in acetone (100 mL, 1 mol) at 0° C. was added 3-iodo-1-propene (3.8 mL, 0.041 mol) and potassium carbonate (5.7 g, 0.041 mol). The reaction mixture was stirred for 1 h at 0° C. then warmed to room temperature overnight. The reaction mixture was worked up by diluting the reaction with water and washing with dichloromethane. The organic phase was washed with a 10% HCl solution, water and brine then dried over magnesium sulfate, filtered and concentrated in vacuo to a greenish-brown oil. Purification of the reaction mixture was accomplished using ISCO chromatography on silica gel (350 g column) using hexane-ethyl acetate (0-100%). The major fractions were combined and concentrated in vacuo to give product, 1-allyloxy-2-nitrobenzene, as a light yellow-green oil (5.4 g, 81%). 1H NMR (CDCl3, 400 MHz) δ 7.83 (d, 1H, J=8.09 Hz), 7.51 (t, 1H, J=8.08 Hz), 7.08 (d, 1H, J=8.33 Hz), 7.03 (t, 1H, J=8.08 Hz), 6.04 (m, 1H), 5.49 (d, 1H, J=17.2 Hz), 5.32 (d, 1H, J=10.6 Hz), 4.69 (d, 2H, J=5.05 Hz).

Provenance & Evidence