Hydrogen Peroxide → 2,4-Dimethoxyphenol

HRID 1457595Notes

Reaction equation

HRID 1457595 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1C=O.OO.S([O-])(O)=[O:21].[K+]>CO>[CH3:6][O:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[OH:21]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 23663620Potassium Bisulfite

Product 1

HCID 5930062,4-DimethoxyphenolYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. sulfuric acid (0.4 ml) was added to a mixed solution comprising 3.3 g of 2,4-dimethoxybenzaldehyde and 30 ml of methanol, and under ice-cooling, 2.93 ml of 30% hydrogen peroxide aqueous solution was added to the mixture. After stirring at room temperature for 4 hours, a 5% aqueous potassium hydrogen sulfite solution was added to the mixture and the solvent was removed under reduced pressure. The residue was extracted with diethyl ether, the extract was washed and dried and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 2.1 g of 2,4-dimethoxyphenol (yield: 69%, state: colorless oily product).

Workup

  1. temperatureunder ice-cooling
  2. customthe solvent was removed under reduced pressure
  3. extractionThe residue was extracted with diethyl ether
  4. washthe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-47141c644cae4fd39b2ba21683089a79
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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