Acetic Acid → HCID 54441028, compound

Participants

Reaction Steps

Triton B (0.2 ml., 40% in MeOH) is added to a stirred solution of 1-(p-chlorophenyl)4,7-diphenyl-1,6-heptadien-3-one (3.72 g., 0.01 mole) in glyme (25 ml.), followed by addition of ethyl acrylate (1.11 g., >0.01 mole). After stirring for 24 hours, glacial acetic acid (0.5 ml.) is added and the solvent removed under reduced pressure. The residue is mixed with a solution of sodium hydroxide (0.80 g., 0.02 mole) in water (15 ml.) and methanol (150 ml.) and stirred for 24 hours. The methanol is removed in vacuo and the residue is dissolved in water (200 ml.). Extraction with ether removes unreacted ketone. Ether is expelled from the aqueous phase and it is acidified to Congo Red with dilute hydrochloric acid. The off-white solid that separates is collected, washed well with water, and air-dried, yield 3 g. Recrystallization from benzene-hexane gives material with m.p. 135°-140°C.

Provenance & Evidence