Iodoethane → HCID 23130247, compound

Participants

Reaction Steps

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

Provenance & Evidence