Methanol → Methyl (3-(trifluoromethyl)phenyl)acetate

Participants

Reaction Steps

A 3.36 g. portion of flaked sodium hydroxide was slurried in 33 ml. of methanol and 1 ml. of water, and the mixture was warmed to dissolve most of the base. It was then cooled to ambient temperature and to it was added over 2-3 minutes 4 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane. The mixture was then stirred under reflux at 70° for 4 hours, and was then cooled to 5°. To it was added about 3 ml. of concentrated sulfuric acid. A little more methanol was added to increase the fluidity of the mixture, and the mixture was stirred under reflux again for 45 minutes more. It was then cooled to ambient temperature, and diluted with about 60 ml. of water. A 35 ml. portion of dichloromethane was added, the layers were separated, and the aqueous layer was extracted with three 25 ml. portions of dichloromethane. All of the organics were combined and washed twice with 15 ml. portions of water, dried over sodium sulfate and concentrated to dryness under vacuum to obtain 2.75 g. of product, found to be 80% pure by vapor phase chromatography.

Provenance & Evidence