Dimethyl Sulfate → Methyl 4-amino-5-chloro-2-hydroxybenzoate

Participants

Reaction Steps

A solution of 4-amino-5-chloro-2-hydroxybenzoic acid (1.88 g, 10 mmoles) in absolute methanol (20 ml) was treated with 25% sodium methoxide/methanol (2.16 g, 10 mmoles), stirred for 30 minutes, and concentrated in vacuo. The solid residue was dissolved in anhydrous acetone (30 ml), treated with dimethyl sulfate (1.64 g, 13 mmoles), and refluxed for 2 hours. The resultant solution was diluted with water (100 ml), and the precipitate was filtered, washed with water, and dried in vacuo to yield 1.75 g (87%) of fine colorless needles. The product was recrystallized from ethyl acetate/hexane, mp 138°-139° C.

Provenance & Evidence