Sodium Iodide → N-(5-Hydroxymethyl-2-methylphenyl)-N-(3-methoxypropyl)acetamide

Participants

Reaction Steps

The solution of 0.892 g of N-(5-hydroxymethyl-2-methylphenyl)acetamide in 8 ml of N,N-dimethylformamide is cooled to 0° C. with stirring and admixed with 0.16 g of sodium hydride dispersion (60%). The mixture is stirred at 0° C. over 30 minutes and subsequently admixed with 0.489 ml of 1-chloro-3-methoxypropane and 60 mg of sodium iodide. The reaction mixture is stirred at 80° C. over 48 hours and poured onto water (50 ml). The mixture is extracted with ethyl acetate (2×50 ml). The organic phases are washed successively with water (2×50 ml) and brine (1×50 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rt=2.73.

Provenance & Evidence