Iodoethane → HCID 23130247, compound

Participants

Reaction Steps

To a suspension of sodium hydride (60% mineral oil: 1.20 g) in dimethylformamide (50 mL) was added 3-hydroxy-4-nitrobenzoic acid methyl ester (4.93 g) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. After addition of ethyl iodide (4.4 g), the solution was stirred at 60° C. overnight, cooled down to room temperature, poured into saturated aqueous ammonium chloride, and extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated aqueous ammonium chloride and saturated brine, dried over sodium sulfate and concentrated to give a solid, which was washed with ethyl acetate-hexane to afford 3-ethoxy-4-nitrobenzoic acid methyl ester (3.30 g) as a pale yellow solid.

Provenance & Evidence