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

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Reaction Steps

Seventy ml. of methanol was combined with 10.7 g. of 86% pure potassium hydroxide and the mixture was stirred for 0.5 hour. To it was added 8.0 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane over 3-4 minutes. The mixture was heated and stirred under reflux at 68° for 4.75 hours, cooled to 10° and made acid with 8 ml. of concentrated sulfuric acid. The mixture was then stirred under reflux for 45 minutes more, and cooled to ambient temperature overnight. To it was then added 100 ml. of water and 50 ml. of dichloromethane. The aqueous layer was extracted with two 40 ml. portions of dichloromethane, and the organics were combined, dried over sodium sulfate and concentrated under vacuum to obtain 5.7 g. of brown oil, found to be 96.6% pure product by vapor phase chromatography. The product was further purified by distillation at 70°-73° under 1.3 torr to obtain 4.89 g. of more highly purified product.

Provenance & Evidence