Acetic Acid → HCID 13923414, compound

Participants

Reaction Steps

2.08 g (52 mmol) of 60% NaH was suspended in 8 ml of N,N-dimethylformamide (DMF) containing 4.20 g (20 mmol) of methyl 3-methoxy-4,5-methylenedioxybenzoate (9), and to this mixture was added dropwise with stirring 2.8 ml (35 mmol) of methyl acetate in 3 ml of dimethylformamide at such a rate that the temperature of the reaction mixture could be maintained at 50°-60° C. After this addition was over, the reaction mixture was kept at 55° C. for one hour, then cooled to room temperature and added with 3.8 ml of acetic acid to stop the reaction. The reaction mixture was added with 30 ml of ice-cold water and extracted with toluene (15 ml×2). The toluene layer was washed with water, further washed with a saturated sodium hydrogencarbonate aqueous solution, then dried over anhydrous magnesium sulfate and concentrated. The residue was washed several times with a small quantity of n-hexane and recrystallized from methanol (10 ml) to obtain 3.61 g of methyl 3-methoxy-4,5-methylenedioxybenzoylacetate (10) (yield: 71.6%). Melting point: 65.5°-66.5° C.

Provenance & Evidence