Water → HCID 23051855, compound

Participants

Reaction Steps

A solution of 1.0 g (3.47 mmol) of (E)-6,6-diethoxy-1-(p-methoxyphenyl)-1-hexen-4-yn-3-one in 4 ml of dioxane and 2 ml of 2.2N aqueous hydrobromic acid was stirred at 30° for 18 hours and subsequently treated with 20 ml of ether and 10 ml of water. The aqueous phase was extracted twice with ethyl acetate. The combined organic fractions were dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on 80 g of silica gel with acetonitrile/water (1:1). The fractions containing the product were extracted with ethyl acetate. The combined ethyl acetate extracts were dried over magnesium sulphate, filtered and evaporated. The residue was recrystallized from ethyl acetate/hexane, whereby there was obtained (E,E)-6-(p-methoxyphenyl)-4-oxo-2,5-hexadienoic acid of melting point 138°-139°.

Provenance & Evidence