Hydrochloric Acid → Methyl 2-(3-nitrophenyl)acetate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-nitrophenylacetic acid (10.4 g, 57.3 mmol) in MeOH (250 ml) at RT was added HCl gas until saturation was achieved. The resulting solution was stirred at 70° C. for 1 h. The reaction was cooled and concentrated under reduced pressure. The semisolid residue was dissolved in Et2O, washed with H2O (2×), satd. NaHCO3 (2×), brine (1×) and dried (MgSO4). Filtration and evaporation provided methyl 2-(3-nitrophenyl)acetate as a low-melting solid (10.7 g, 96% yield), which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 8.14-8.04 (m, 2H), 7.64-7.58 (m, 1H), 7.47 (brt, J=8.10 Hz, 1H), 3.72 (s, 2H), 3.68 (s, 3H); MS (ESI) m/z: 196.0 (M+H+).

Provenance & Evidence