Ethyl Acetoacetate → HCID 20155632, compound

Participants

Reaction Steps

Ethyl acetoacetate (6.85 g, 0.0526M) was added at 70° to a solution of sodium (1.21 g, 0.0526M) dissolved in ethanol (150 ml). After a few minutes [2,3-dichloro-4-(3-phenyl-1-oxo-2-propenyl)phenoxy]acetic acid (8.7 g, 0.0248M) was added and the suspension was stirred at reflux for 3 hours, cooled and concentrated under vacuum. The residue was taken up in water, acidified with hydrochloric acid and extracted with methylene chloride. The organic extracts were washed with water dried over MgSO4 and concentrated. The residue was triturated with toluene and the solid that crystallized filtered. The crude product was taken up in butyl chloride and filtered. The filtrate was concentrated under vacuum and the residue recrystallized from toluene to give ethyl 4-[4-(carboxymethoxy)-2,3-dichlorophenyl]-2-oxo-6-phenyl-3-cyclohexene-1-carboxylate, m.p. 91° C.

Provenance & Evidence