1-Butanol → Butyl [3-(trifluoromethyl)phenyl]acetate

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Reaction Steps

To 5.6 g. of potassium hydroxide of the grade described above was added 25 ml. of butanol, and the mixture was stirred for 15 minutes. To it was added dropwise 2.8 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane, and the mixture was stirred under reflux for 3.75 hours. It was then cooled to 5°, and to it was added dropwise 6 ml. of concentrated sulfuric acid. The mixture was then stirred under reflux for 30 minutes and cooled overnight. It was then reheated to reflux, and about 22 ml. of butanol and water was distilled away. The mixture was then cooled again, and diluted with about 50 ml. of water. The aqueous layer was separated and extracted with three 25 ml. portions of dichloromethane. The organic layers were combined, washed with 1 N sodium hydroxide, dried over sodium sulfate and evaporated under vacuum to obtain 3.0 g. of impure product. The product was dissolved in 30 ml. of dichloromethane, washed with water, dried over sodium sulfate and concentrated under vacuum again to obtain 2.67 g. of product, found to be 83% pure by vapor phase chromatography.

Provenance & Evidence