Synthesis
GENERAL STEPS: The synthesis of ethyl 3,4-dimethoxybenzoylacetate from 3,4-dimethoxyacetophenone and diethyl carbonate was carried out as follows: first, 3,4-dimethoxyacetophenone (0.05 mol) was dissolved in toluene (50 mL) and then added slowly and dropwise to a solution containing diethyl carbonate (0.10 mol) and sodium hydride (0.15 mol, 60% mineral oil dispersion) (0.15 mol, 60% mineral oil dispersion). The reaction mixture was stirred at room temperature and heated to reflux for 30 minutes. Upon completion of the reaction, the mixture was poured into ice water, acidified with glacial acetic acid and subsequently extracted with ethyl acetate (3 x 100 mL). The organic phases were combined and dried with anhydrous magnesium sulfate. After removal of solvent by distillation under reduced pressure, the crude product was purified by silica gel column chromatography using dichloromethane as eluent to afford the target product ethyl 3,4-dimethoxybenzoylacetate. All the synthesized compounds were subjected to structural confirmation by 1H NMR, 13C NMR, IR and mass spectrometry.
References
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