Ethyl Acetoacetate → [(2,3-Dichloro-5'-oxo[2',3',4',5'-tetrahydro[1,1'-biphenyl]]-4-yl)oxy]acetic acid

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Reaction Steps

To a stirred solution of sodium methoxide (0.5 g, 0.009 moles) in ethanol (40 ml) and ethyl acetoacetate (0.9 ml) was added [2,3-dichloro-4-(3-dimethylamino-1-oxopropyl)phenoxy]acetic acid (0.95 g, 0.0027 mole). The reaction mixture was heated at reflux for 21/2 hours then the solvent was distilled at reduced pressure. The residue was dissolved in water, acidified with hydrochloric acid, extracted with ether, washed with water, dried over magnesium sulfate and evaporated at reduced pressure to give 50 mg of [2,3-dichloro-4-(3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid which melted at 197°-198° C. after purification by thin layer chromatography on silica gel (CH2Cl2 :THF:methanol; 50:1:1).

Provenance & Evidence