Ethyl 2-methylacetoacetate → HCID 13749104, compound

Participants

Reaction Steps

To a stirred solution of sodium methoxide (3.5 g, 0.065 mole) in ethanol (100 ml) and ethyl-2-methylacetoacetate (6.6 ml) was added [2,3-dichloro-4-(3-dimethylamino-1-oxopropyl)phenoxy]acetic acid hydrochloride (7.4 g, 0.021 mole). The reaction mixture was heated at reflux for 3 hours then the solvent was distilled at reduced pressure, treated with 100 ml of 2% sodium hydroxide, heated on a steam bath for 11/2 hours, then acidified, extracted with ether, washed with water, dried over magnesium sulfate and evaporated at reduced pressure. The residue was triturated with 100 ml of hot toluene, filtered, and dried to give 0.9 of [2,3-dichloro-4-(4-methyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 183°-185° C. after recrystallization from 30 ml of toluene.

Provenance & Evidence