Methanol → Methyl 4-aminobenzoate

Participants

Reaction Steps

2.1 g (15.6 mmol) of 4-aminobenzoic acid was dissolved in anhydrous MeOH, added 14.47 g (123.3 mmol) of thionyl chloride dropwise under N2 while stirring at rt. After dtiring for four hours, solvents were removed and redissolved in 100 mL EtOAc and 40 mL of saturated NaHCO3 aq, stirred 30 min, separated and washed with 3×20 mL water. Organics were dried yielding 2.17 g (yield 92.1%) of methyl 4-aminobenzoate. 1H NMR (300 MHz, CDCl3): 7.88 (2H, d, J=8.6 Hz), 6.66 (2H, d, J=8.6 Hz), 4.19 (2H, broad s), 3.88 (3H, s). 13C NMR (300 MHz, CDCl3): 167.8 (C═O), 151.4 (Cq), 131.9 (2×CH), 120.0 (Cq), 113.8 (2×CH), 50.9 (CH3).

Provenance & Evidence