Dimethyl Carbonate → HCID 14501062, compound

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Reaction Steps

A mixture of 1-[4,5-(methylenedioxy)-2-(phenylmethoxy)phenyl]ethanone (5.4 g, 0.02 mol), sodium hydride (1.6 g of 60% sodium hydride, 0.04 mol) and dimethylcarbonate (18 g, 0.2 mol) was heated to 70°-75° C. for 20 minutes. After evaporating the excess dimethylcarbonate under reduced pressure, the residue was acidified with 10% HCl solution and extracted with ether. The ether solution was washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was filtered through silica gel using chloroform as eluent to afford 5.99 g (91.3%) of methyl 4,5-(methylenedioxy)-β-oxo-2-(phenylmethoxy)benzenepropanoate mp (EtOH) 86°-86.5° C.; IR (KBr) 1750 (ester), 1652 (carbonyl) cm-1 ; NMR (CDCl3, 90 MHz) δ, 3.61 (S, 3H, CO2CH3), 3.92 (S, 2H, CH2CO2CH3), 5.11 (S, 2H, CH2Ph), 5.98 (S, 2H, OCH2O), 6.54 (S, 1H, ArH), 7.39 (S, 5H, CH2Ph), 7.41 (S, 1H, ArH). Anal. calcd. for C18H16O6 : C, 65.85; H, 4.91. Found: C, 65.92; H, 5.11.

Provenance & Evidence