Diphenyl Ether → 2-allyl-4-nitrophenol

Participants

Reaction Conditions

Reaction Steps

A mixture of allyl 4-nitrophenyl ether (78 g) and diphenyl ether (150 ml) was heated at 250° C. for 30 minutes. The reaction mixture was cooled to ambient temperature, and partitioned between diethyl ether and 2M aqueous sodium hydroxide solution. The aqueous layer was separated and acidified to pH3 with concentrated hydrochloric acid. The aqueous mixture was extracted with ethyl acetate the ethyl acetate extract dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (Merck 7736) using a gradient of 0% to 20% methanol in dichloromethane as eluent to give 2-allyl-4-nitrophenol (21.4 g); microanalysis, found: C, 60.6; H, 5.1; N, 7.9%; C9H9 NO3 requires: C, 60.3; H, 5.06; N, NMR): 3.36(2H,d), 5.1(2H,m), 5.98(1H,m), 6.97(1H,d), 8.0(2H,m); m/z 197 (M+NH4).

Provenance & Evidence