Water → Methyl 4-(2-(dimethylamino)ethoxy)benzoate

Participants

Reaction Steps

Methyl 4-hydroxybenzoate (10 g, 66 mmoles) was dissolved in N,N-dimethylformamide (200 mL). Potassium carbonate (45 g, 0.33 moles) and 2-chloro-N,N-dimethylethylamine hydrochloride (14.2 g, 99 mmoles) were added and the resulting mixture was stirred vigorously at room temperature for 7 days. More 2-chloro-N,N-dimethylethylamine hydrochloride (3 g, 20 mmoles) was added and stirring at room temperature was continued for 2 days. The reaction mixture was poured into water (600 mL) and extraction with ethyl acetate (2×200 mL), washing of the combined organic phases with water (200 mL), drying over MgSO4 and evaporation afforded 11.9 g (81%) of methyl 4-(2-dimethylaminoethoxy)benzoate as an oil.

Provenance & Evidence