Phenethyl bromide → 5-Phenyl-2-pentanone

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Reaction Steps

According to reference F. C. Montgomery, W. H. Saunders, Jr. J. Org. Chem. 1976, 41, 2368-72, 7.6 g of sodium are added to 200 ml of absolute ethanol. Once the sodium has dissolved, 43 g (0.33 mol) of ethyl acetoacetate are added dropwise within an hour, the mixture refluxed for 1 hour, 65 g of 2-phenylethyl bromide are slowly added dropwise and the mixture is refluxed again (21 hours). After cooling and filtration, the mixture is distilled. The product is first heated for 5 h to 90° C. with 350 ml of 5% sodium hydroxide, then stirred for 5 hours at the same temperature with 150 ml of 50% sulfuric acid. After cooling, the product is left to stand for 48 hours, extracted with diethyl ether, the combined extracts are dried over sodium sulfate and 3a is finally obtained in good yield by distillation (b.p.: 132-134° C., 2.3 103 Pa (17 Torr)).

Provenance & Evidence