Acetyl chloride → 6-Methoxy-2-naphthylacetic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1.6 g. of 2-methoxynaphthalene, 1.6 g. of acetyl chloride, and 20 ml. of nitrobenzene, there are added 4.0 g. of aluminum chloride. The resulting mixture is stirred for 48 hours at 25°C; then it is washed with water until free of chloride ion. The mixture is dried over sodium sulfate and evaporated under reduced pressure. The residue, 2-acetyl-6-methoxynaphthalene, is refluxed in 2 ml. of morpholine containing one-half gram of sulfur for 2 hours; the reaction mixture is then filtered and evaporated. The resulting reaction derivative is extracted with diethyl ether; the extracts are combined and evaporated. The residue is refluxed in 10 ml. of concentrated hydrochloric acid for 2 hours, cooled to 25°C, and neutralized with aqueous sodium hydroxide. The mixture is then extracted with ether and the extracts are combined, washed with water to neutrality, dried and evaporated to yield 2-(6-methoxy-2-naphthyl)acetic acid.

Provenance & Evidence