Potassium Hydroxide → Benzeneacetic acid, butyl ester

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Reaction Steps

The process of Example 4 was followed, using 45 ml. of butanol, 12.5 g. of potassium hydroxide, and 4.6 g. of 1,1,1-trichloro-2-phenylethane. The reflux was carried on for 8 hours, at 110°. The product was 3.85 g. of rather impure oil, apparently containing some of the 2-chloro-2-butoxystyrene impurity, which was converted to desired product by adding 8 ml. of butanol and 40 ml. of 1 N hydrochloric acid and stirring the mixture for 20 minutes. The layers were separated, and the aqueous was extracted with two 30 ml. portions of diethyl ether. The organics were combined and washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under vacuum to obtain 4.2 g. of partially purified product, 77% pure by vapor phase chromatography.

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