Dimethylformamide → Methyl 3-methoxy-4-nitrobenzoate

Participants

Reaction Steps

To a mixture of 3-hydroxy-4-nitrobenzoic acid (203 g, 1.109 mol) and K2CO3 (345 g, 2.496 mol) in DMF (3000 mL) was added drop wise CH3I (400 g, 2.817 mol) at ambient temperature. The mixture was stirred at ambient temperature for 13 h. TLC (EtOAc: Petroleum ether 1:4) indicated the reaction was complete. Most of the solvent was removed under reduced pressure and the residue was diluted with water (2 L). Then the mixture was extracted with EtOAc (2 L×3). The combined organic layers were washed with water (1L×3), dried over Na2SO4 and concentrated under reduced pressure to yield the desired ester (172 g, 73.5%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.848-7.827 (d, 2H), 7.759 (s, 1H), 7.705-7.681 (d, 1H), 4.018 (s, 3H), 3.969 (s, 3H).

Provenance & Evidence