Hydrogen Peroxide → 4-Methoxyphenol

HRID 370839Notes

Reaction equation

HRID 370839 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](C=O)=[CH:5][CH:4]=1.OO.[OH:13]S(O)(=O)=O.[O-]S([O-])=O.[Na+].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([OH:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 312444-Methoxybenzaldehyde

Product 1

HCID 90154-Methoxyphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 13.6 g 4-methoxybenzaldehyde and 1.1 equivalents 50 percent H2O2 in 55 ml methanol at about 20° C. is added 0.10 equivalent of 98 percent H2SO4. The mixture is refluxed for about 1.5 hours, then Na2SO3 is added to destroy excess H2O2. Then, NaHCO3 is added to neutralize any acid. The solvent is removed under reduced pressure. The resulting solid is taken up in about 50 ml CH2Cl2, is dried over Na2SO4, and is filtered. The sol-vent is removed under reduced pressure from the filtrate giving approximately a 94 mole percent yield of 4-methoxyphenol as is determined by nuclear magnetic resonance and gas chromatography.

Workup

  1. temperatureThe mixture is refluxed for about 1.5 hours
  2. customto destroy excess H2O2
  3. additionThen, NaHCO3 is added
  4. customThe solvent is removed under reduced pressure
  5. dry with materialis dried over Na2SO4
  6. filtrationis filtered
  7. customThe sol-vent is removed under reduced pressure from the filtrate

Sources & evidence

ORD record
ord-5f0469ba3056465f97d665074f999699
Source dataset
uspto-grants-1985_07
Patent number
US04528394

Reaction notes

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