3-acetylacrylate and 25.4 g. (0.14 mole) of ethyl a-bromopropionate in 100 cc. of a mixture of dry benzene and toluene, which contained equivalent amounts of benzene and toluene, was added dropwise with stirring. The reaction started after gentle warming; however, the reaction mixture soon set to a gel and failed to reflux spontaneously. The mixture was then maintained at reflux by means of an oil-bath, and the remainder of the reactants was added dropwise with stirring. Stirring and refluxing were continued for three hours after all the benzene-toluene solution had been added.The reaction mixture was poured into iced sulfuric acid, and the benzene-toluene layer was separated. The aqueous layer was extracted with ether. The ether and benzene-toluene extracts were combined, washed with 5% sodium carbonate solution, and dried over anhydrous sodium sulfate. Removal of the solvents under diminished pressure left an oil which was distilled: colorless liquid, b. p. 121-122°(2 mm.); %> 1.4579; yield, 10.5g. (30%).
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