Methanol → Methyl 2-(4-aminophenyl)acetate

Participants

Reaction Steps

To a suspension of 4-amino-phenyl acetic acid (5 g, 33 mmol) in methanol (20 mL) was added concentrated sulfuric acid (2 mL) dropwise. The reaction mixture was stirred at reflux for 1.5 h, then concentrated in vacuo. The residue was partitioned between 1 M aqueous potassium carbonate and diethyl ether. The organic layer was washed with 1 M aqueous potassium carbonate, water, then dried over sodium sulfate and filtered. The filtrate was concentrated and dried in vacuo to give 4.65 g of the product as a dark yellow oil. 1H NMR 500 MHz (DMSO) δ 3.43 (s, 2H), 3.57 (s, 3H), 4.97 (s, 2H), 6.49 (d, 2H), 6.88 (d, 2H); MS (m/z) 166 [M+H+]+.

Provenance & Evidence