Hydrochloric Acid → Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

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Reaction Steps

Ethyl 4,5-dimethoxy-2-nitrobenzoate (10.22 g, 40.04 mmol) was refluxed in 20% aqueous NaOH (50 mL) for 2 days. The solution was cooled, acidifed to pH 2 using concentrated HCl, and the resulting solid filtered, washed with water and dried. The solid was dissolved in methanol (90 mL) and thionyl chloride (3.1 mL, 42.75 mmol) cautiously added. After refluxing for 3 days, the solution was cooled, concentrated and diluted with dichloromethane (280 mL). The organic phase was washed with water (200 mL) and the aqueous layer further extracted with dichlormethane (100 mL). Organic layers were combined, dried (MgSO4) and concentrated to give the title compound as a yellow solid (6.00 g, 66%).

Provenance & Evidence