Water → 2-(4-Chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one

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Reaction Steps

100 ml of water, followed by 28 ml of 10% strength aqueous sodium hydroxide solution, were added to a stirred solution of 22.6 g (0.1 mol) of 1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one and 21.4 g (0.2 mol) of 3-pyridinealdehyde in 500 ml of methanol. The solution was subsequently stirred at room temperature for 4 days, the methanol was removed in vacuo and the aqueous residue was taken up in ether. The aqueous phase was separated off, the organic phase was extracted three times with 1 N hydrochloric acid and the hydrochloric acid extracts were neutralized with solid sodium bicarbonate and extracted three times with ethyl acetate. 22.8 g (72% of theory) Of 2-(4-chlorophenoxy)-4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one of melting point 74°-76° C. were obtained from the ethyl acetate phase.

Provenance & Evidence