(2-Benzoylethyl)trimethylammonium iodide → 1-Phenyl-2-propen-1-one

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Reaction Steps

N-(2-benzoylethyl)-N,N,N-trimethylammonium iodide (5.0 g) was suspended in water (400 ml) and the mixture passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) and the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath. The ether phase was separated and the aqueous extracted with ether (3×150 ml). The pooled organic phase was dried over anhydrous sodium sulphate and evaporated to dryness, affording phenylvinyl ketone as a colourless oil (1.95 g; 94% yield) in high purity, according to the 1H NMR spectrum; cf ref.15, where a yield of 51% was obtained.

Provenance & Evidence