1-Butanol → Butyl (2-chlorophenyl)acetate

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Reaction Steps

Forty ml. of butanol was added to 9.2 g. of potassium hydroxide, which contained about 14% water, and was stirred at ambient temperature for 1 hour. To the mixture was added in one portion, 4 g. of 1,1,1-trichloro-2-(2-chlorophenyl)ethane. The mixture was heated to reflux and stirred at that temperature for 6 hours, and was cooled overnight to ambient temperature. It was then poured into 125 ml. of 1 N hydrochloric acid and stirred at ambient temperature for 30 minutes. The layers were then separated, and the aqueous layer was washed twice with about 60 ml. portions of diethyl ether. The organics were combined, and washed with two 25 ml. portions each of 10% sodium bicarbonate solution, water, and saturated sodium chloride solution. The washed organic portion was then dried over sodium sulfate, filtered and evaporated under vacuum to obtain 3.23 g. of crude product, which was found to be 87.6% pure by chromatography. A 2.5 g. portion of the above was distilled at 135° and 8 torr to obtain 1.9 g. of purified product, 97.0% pure by chromatography.

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