Water → 3-isopropoxynitrobenzene

Participants

Reaction Steps

A mixture of 3-nitrophenol (20 g; 144 mmol), 2-iodopropane (21.45 m 36.6 g; 216 mmol) and potassium carbonate (23.8 g; 172 mmol) in dimethylformamide (100 ml) was stirred at 50° for 2 h and then the temperature was increased to 70° for a further 2 h. More 2-iodopropane (7.15 ml; 72 mmol) was added and stirring at 70° continued for a further 1.5 h whereupon the mixture was poured into water (400 ml) and extracted with ethyl acetate (2×400 ml). The combined organic extracts were washed with sodium hydroxide (300 ml), then saturated brine (300 ml), dried and evaporated. The residue was chromatographed on silica (675 g) using petroleum ether (40°-60°)-ethyl acetate (10:1) as eluant to give the title compound (Intermediate 43; 22.37 g; 86%) as a yellow oil.

Provenance & Evidence