Methyl iodide → (RS)-Naproxen methyl ester

Participants

Reaction Steps

To a mixture of 22 g. of methyl 2-(6-methoxy-2-naphthyl)acetate (prepared by treating 20.5 g. of 2-(6-methoxy-2-naphthyl)acetic acid with 4.5 g. of diazomethane in ether), and 2.5 g. of sodium hydride in 150 ml. of 1,2-dimethoxyethane; 25 g. of methyl iodide are added. The reaction mixture is allowed to stand for several hours; then it is diluted with ethanol followed by water and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered and evaporated to yield methyl 2-(6-methoxy-2-naphthyl)propionate.

Provenance & Evidence