Methanol → Methyl 2-(2-nitrophenyl)acetate

Participants

Reaction Steps

To a solution of 2-nitrophenylacetic acid (2.00 kg) in methanol (4 l) at room temperature is added concentrated sulfuric acid (71.0 ml) all at once. The solution is stirred and refluxed for 6 hours, then allowed to stand at room temperature overnight. After cooling in an ice bath to 7°, the solution is adjusted to pH 8 by the addition of concentrated ammonium hydroxide (150 ml), keeping the temperature below 10°. The solution is concentrated in vacuo to a volume of 2 l and is then admixed with dichloromethane (2.5 l). The combined solution is washed with water (2×500 ml) and brine (500 ml), dried over anhydrous magnesium sulfate, and evaporated to yield crude product which is distilled to give methyl 2-nitrophenylacetate, b.p. 116°-131° (0.2 mm Hg).

Provenance & Evidence