Potassium Hydroxide → HCID 23051850, compound

Participants

Reaction Steps

A solution of 5.3 g (21.7 mmol) of methyl (E)-6-(4-methoxyphenyl)-4-oxo-5-hexen-2-ynoate in 70 ml of tetrahydrofuran was treated at 0° within 15 minutes with 48.6 ml (26 mmol) of a 3% aqueous potassium hydroxide solution. The reaction mixture was stirred at 0° for 10 minutes, then diluted with 100 ml of water and extracted once with 100 ml of ether. The organic phase was discarded. The aqueous phase was adjusted to pH 1 by the careful addition of 1N hydrochloric acid and extracted twice with ether. The combined organic phases were washed with water, dried over sodium sulphate and concentrated. Crystallization of the residue from ether/hexane yielded (E)-6-(4-methoxy-phenyl)-4-oxo-5-hexen-2-ynoic acid of melting point 98°-100°.

Provenance & Evidence