Acetone → HCID 71278892, compound

HRID 1749719Notes

Reaction equation

HRID 1749719 reaction equation
O[C:2]1C(C)=[CH:9][C:8]([OH:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S([O:18][CH3:19])(OC)(=O)=O.[C:20](=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].[CH3:32][C:33](C)=[O:34]>>[CH3:20][O:12][C:8]1[CH:7]=[C:3]([CH3:2])[C:4]([O:6][CH2:32][C:33]([O:18][CH3:19])=[O:34])=[C:27]([CH:9]=1)[C:28]([O:30][CH3:31])=[O:29]

Participants

6

Reactant 5

HCID 180Acetone2×HCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate2×HCID 60984Methyl bromoacetateHCID 144020332,5-Dihydroxy-3-methylbenzoic acid

Product 1

HCID 71278892HCID 71278892, compoundYield 63%

Procedure

2,5-Dihydroxy-3-methylbenzoic acid (4.7 g, 29 mmol) was added successively with acetone (40 mL), dimethyl sulfate (9.0 g, 71 mmol), and potassium carbonate (10 g, 72 mmol), and the mixture was stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure, the residue was added with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was successively added with acetone (50 mL), potassium carbonate (1.0 g, 72 mmol), and methyl bromoacetate (6.6 g, 43 mmol), and then the mixture was refluxed for 8 hours by heating. The reaction mixture was filtered through Celite, and then the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50)) to obtain methyl 5-methoxy-2-(2-methoxy-2-oxoethoxy)-3-methylbenzoate (4.9 g, 63%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with ethyl acetate
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. temperaturethe mixture was refluxed for 8 hours
  7. temperatureby heating
  8. filtrationThe reaction mixture was filtered through Celite
  9. customthe solvent was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. washthe organic layer was washed successively with water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50))

Sources & evidence

ORD record
ord-a59c6d46701d409aa99501e3d45fd110
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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