1,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl ester → HCID 358344, compound

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Reaction Steps

Dimethyl 3-nitrophthalate (4.8 g, 20 mmol) was added to a cold solution of sodium methoxide (2.61 g, 48.3 mmol) in dry hexamethylphosphoric triamide (75 ml). The resulting dark solution was gradually brought to room temperature and the reaction mixture was stirred for 44 hrs. It was then diluted with water (125 ml) and extracted with benzene. (This extract contained a variable quantity of dimethyl 3-methoxyphthalate. The aqueous layer was acidified with hydrochloric acid and extracted with benzene. The combined organic layers were washed with water (5×30 ml) and then brine (1×15 ml), dried over sodium sulfate, filtered and evaporated to give 3.25 g (75%) of 2-carbomethoxy-3-methoxybenzoic acid, mp 140°-141° C. (benzene). Identity was confirmed by mixture mp, co-chromatography and spectroscopic comparison with an authentic sample. 1H NMR (CDCl3) δ 3.86 (3H, s, ArCO2CH3), 3.93 (3H, s, ArOCH3), 7.13 (1H, dd, J=8,2 Hz, ArH4), 7.43 (1H, t, J=8 Hz, ArH5), 7.68 (1H, dd, J=8,2 Hz, ArH6, 10.50 (1H, broad s, ArCO2H); IR (KBr) 3200 (br), 2960, 1740, 1690, 1585, 1475, 1310, 1050 cm-1 , etc.; mass spectrum m/e (rel. intensity) 211 (m+ +1,5%), 210 M+, 30%), 193 (M+ -OH, 2%), 180 (M+ -2CH3, 100%), 179 (M+ -OCH3, 10%), etc.

Provenance & Evidence