Sulfuric Acid → 5-Ethoxycarbonyloxy-2-nitrobenzoic acid

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Reaction Steps

A stirred mixture of 3-formyl-4-nitrophenyl ethyl carbonate (33.1 g, prepared as described in J. Chem. Soc., 1925, 1195), potassium permanganate (17.0 g), acetic acid (33 ml) and acetone (330 ml) was cooled to keep the temperature below 50°, then allowed to stand at room temperature for a further 45 minutes. Dilute sulphuric acid and chloroform were added and the mixture decolorised with sodium metabisulphite. The organic layer was extracted with sodium bicarbonate solution and the extracts acidified with dilute hydrochloric acid to give 3-carboxy-4-nitrophenyl ethyl carbonate (23.2 g, m.p. 132°-7°).

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