Water → Butyl [3-(trifluoromethyl)phenyl]acetate

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Reaction Steps

To a suspension of 5.6 g. of potassium hydroxide, containing 14% of water, in 35 ml. of dried butanol was added 4.0 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane over about 2 minutes. The mixture was stirred under reflux for 5 hours, was cooled, and was made acid with 6 ml. of concentrated sulfuric acid. The mixture was heated to reflux with a distillation head on the flask, and about 11 ml. of butanol-water azeotrope was removed. Ten ml. of butanol was added back to the flask, and the mixture was cooled overnight to ambient temperature. It was then poured into 150 ml. of water, and the aqueous layer was extracted with two 40 ml. portions of dichloromethane. The organics were combined, and washed twice with 30 ml. portions of water. The organics were then dried over sodium sulfate, and concentrated under vacuum to obtain 4.0 g. of oily product, which was redissolved in 30 ml. of dichloromethane and washed twice with 10 ml. portions of water. The organic solution was dried over sodium sulfate and evaporated under vacuum to obtain 3.4 g. of product, found to be 94.5% pure by vapor phase chromatography.

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