3,5-Dinitrobenzoic acid → 3-Methoxy-5-nitrobenzoic acid

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Reaction Conditions

Reaction Steps

3,5-Dinitrobenzoic acid (866 mg) was dissolved in 1 M LiOMe in MeOH (1.3 mL), then evaporated to dryness. The resulting solid was dissolved in 30 mL of hexamethyl phosphoramide and heated at 80° C. for 16 h. The mixture was then cooled and poured onto a mixture of crushed ice (250 g) and 6NH2SO4 (42 mL). The mixture was extracted with ether, and the extract was washed with water and brine, then dried over MgSO4, filtered and evaporated to yield an orange solid. Filtration through silica gel using 9:1 CH2Cl2/MeOH followed by evaporation provided 624 mg of product. 1H-NMR (d6-acetone): δ 8.36 (1H, dd, J=1.6, 2.0 Hz), 7.97 (1H, t, J=2.0 Hz), 7.91 (1H, dd, J=1.6, 2.0 Hz), 4.03 (3H, s).

Provenance & Evidence