Methanol → Methyl 2-(4-aminophenyl)acetate

Participants

Reaction Steps

To a suspension of 4-aminophenylacetic acid (7.4 g; 59.0 mmol) in ca. 90 ml of methanol, was added ca. 6.0 ml of concentrated sulfuric acid. After refluxing the brown solution for 2.5 hrs, it was concentrated to a dark oil. The oil was diluted with water and basified with 10 wt % NaHCO3 to pH 9 and extracted with ethyl acetate. The organic layer was washed with water, brine and dried with Na2SO4. Evaporation in vacuo afforded 5.0 g of methyl 4-aminophenylacetate as a dark oil.

Provenance & Evidence