Dimethyl Carbonate → HCID 14501062, compound

HRID 231133Notes

Reaction equation

HRID 231133 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

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 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.

Workup

  1. temperaturewas heated to 70°-75° C. for 20 minutes
  2. customAfter evaporating the excess dimethylcarbonate under reduced pressure
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe crude product was filtered through silica gel

Sources & evidence

ORD record
ord-23ca2fdadaf94f9d9cad959881de56da
Source dataset
uspto-grants-1989_07
Patent number
US04845121

Reaction notes

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