Acrolein → 2,6-dimethyl-2-cyclohexen-1-one

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Reaction Steps

19.6 g (0.35 mole) of freshly distilled acrolein is added dropwise at a maximum of 50° C., with ice-cooling, to a solution of 27.8 g (0.2 mole) of N-(3-pent-2-enyl)-pyrrolidine in 50 ml of benzene. After completion of the addition, the mixture is stirred overnight at room temperature; it is subsequently heated for 2 hours at 50°-55° C. and then concentrated by evaporation. The oil remaining is dissolved in 250 ml of 20% hydrochloric acid and the solution is stirred overnight. Extraction is then performed five times with ether; the combined extracts are dried over magnesium sulphate and the ether is distilled off. The crude 2,6-dimethyl-cyclohex-2-en-1-one remaining is purified by vacuum distillation. There is obtained 14.8 g (60% of theory) of 2,6-dimethyl-cyclohex-2-en-1-one, b.p. 62°-64° C./ 10 Torr.

Provenance & Evidence