Toluene → HCID 11448389, compound

HRID 430738Notes

Reaction equation

HRID 430738 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8]C)=O.[H-].[Na+].[C:21]1(C)[CH:26]=CC=C[CH:22]=1>>[CH3:1][O:2][C:3]1[C:4]2[O:13][C:14]([CH2:26][CH:21]=[CH2:22])([C:15]([O:17][CH3:18])=[O:16])[C:6](=[O:8])[C:5]=2[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24758Sodium hydrideHCID 4141042Methyl 3-methoxy-2-(2-methoxy-2-oxoethoxy)benzoate

Product 1

HCID 11448389HCID 11448389, compoundYield 92%

Procedure

Methyl 3-methoxy-2-(methoxycarbonylmethoxy)benzoate (19.39 g) was dissolved in toluene (200 ml). To this solution, sodium hydride (3.36 g) was added and the resultant was stirred at room temperature for 20 minutes, followed by refluxing the mixture for 2 hours. Toluene was evaporated off under reduced pressure and the residue was dissolved in DMF (150 ml). To this solution, acetic acid (2 ml) was added and the solvent was evaporated off under reduced pressure. The residue was dissolved in toluene (200 ml) and the solution was refluxed for 1 hour. The reaction solution was cooled to room temperature and poured into water (150 ml), followed by separating the organic layer. The aqueous layer was extracted with ethyl acetate (100 ml) and the organic layers were combined. The resultant was washed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine, followed by drying the resultant over sodium sulfate. After removing sodium sulfate by filtration, the solvent was evaporated off, and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desire compound (18.42 g, yield: 92%).

Workup

  1. temperatureby refluxing the mixture for 2 hours
  2. customToluene was evaporated off under reduced pressure
  3. dissolutionthe residue was dissolved in DMF (150 ml)
  4. additionTo this solution, acetic acid (2 ml) was added
  5. customthe solvent was evaporated off under reduced pressure
  6. dissolutionThe residue was dissolved in toluene (200 ml)
  7. temperaturethe solution was refluxed for 1 hour
  8. temperatureThe reaction solution was cooled to room temperature
  9. additionpoured into water (150 ml)
  10. customby separating the organic layer
  11. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  12. washThe resultant was washed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine
  13. dry with materialby drying the resultant over sodium sulfate
  14. customAfter removing sodium sulfate
  15. filtrationby filtration
  16. customthe solvent was evaporated off
  17. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-3f80aa0b6adb4d128d38fe2ab8487ebb
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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