Ethanol → Ethyl 2-methyl-5-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-5-nitrobenzoic acid (27.6 mmol, 5 g) in ethanol (100 mL), sulfuric acid (138 mmol, 7.36 ml) was added slowly and stirred overnight at 80° C. The reaction mixture was neutralized with saturated solution of Na2CO3, extracted with diethyl ether (3×), organic layers were washed with brine, dried and concentrated under reduced pressure to yield crude product ethyl 2-methyl-5-nitrobenzoate 101 (5.4 g, 95%). NMR (400 MHz, CDCl3) 1.44 (t, J=7.0 Hz, 3H), 2.72 (s, 3H), 4.42 (q, J=7.04 Hz, 2H), 7.43 (d, J=8.6 Hz, 1H), 8.23 (dd, J=8.6 Hz and 2.7 Hz, 1H), 8.76 (d, J=2.7 Hz, 1H).

Provenance & Evidence