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

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Reaction Steps

Fifty ml. of butanol was added to 11.2 g. of potassium hydroxide, reagent grade, containing about 14% of water, and the mixture was stirred until most of the potassium hydroxide had dissolved. To the mixture was then added 5.6 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane, dropwise over a period of 5 minutes. The mixture warmed exothermically to about 35° as the addition was made. The mixture was then heated to reflux, about 115°, and was stirred under reflux for 6 hours, cooled to ambient temperature and allowed to stand for about 3 days. It was then poured into 60 ml. of 5 N sulfuric acid, and the layers were separated. The lower, aqueous layer was extracted with about 50 ml. of dichloromethane, the organic portion was combined with the upper, organic layer, and the combined organics were washed with 20 ml. of 1 N sodium hydroxide and dried over sodium sulfate. The volatile portions were evaporated under vacuum to obtain 4.3 g. of crude product.

Provenance & Evidence