Ethanol → HCID 20226828, compound

Participants

Reaction Steps

To a stirred solution of sodium (0.95 g, 0.0414 mole) in ethanol (75 ml) and ethyl acetoacetate (5.38 g, 0.0414 mole) was added [3-chloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid (4.94 g, 0.0184 mole). The reaction mixture was heated at reflux for 3 hours. 1N sodium hydroxide (10 ml) and 55 ml of water was added and refluxing was continued for 11/2 hours, then the solvent was distilled at reduced pressure. The residue was acidified, extracted with ether, washed with water, dried over magnesium sulfate to give 4.1 g of [3-chloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 138°-140° C. after recrystallization from butyl chloride and methanol.

Provenance & Evidence