Dimethyl Carbonate → HCID 14501062, compound

Reaction equation

[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=2)[O:2]1.[H-].[Na+].[CH3:23][O:24][C:25](=O)[O:26]C>>[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:6]([C:10](=[O:12])[CH2:11][C:25]([O:24][CH3:23])=[O:26])[CH:7]=2)[O:2]1

Participants

Reactant 3

HCID 12021Dimethyl Carbonate

HCID 24758Sodium hydride

HCID 13193691HCID 13193691, compound

Product 1

HCID 14501062HCID 14501062, compoundYield 91.3%

Procedure

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.