Dichloromethane → 2-(Methoxymethyl)-4-nitroaniline

Participants

Reaction Steps

2-Hydroxymethyl-4-nitroaniline (1.0 g, 5.75 mmol) is suspended in petroleum ether (10 mL). Sodium hydroxide solution (50%, 618 mg, 15.46 mmol) and benzyltriethylammonium chloride (20 mg) are added with stirring. Dimethyl sulfate (728 uL, 7.7 mmol) is added and the reaction mixture is stirred at room temperature for 16 h. Dichloromethane (50 mL) and water (25 mL) are added and the layers are separated. The organic layer is washed with saturated NaHCO3 and evaporated affording 440 mg of 2-methoxymethyl-4-nitroaniline (Ma) in 82% purity.

Provenance & Evidence