Hydrogen Peroxide → 5-Bromo-2-methoxyphenol

HRID 2379577Notes

Reaction equation

HRID 2379577 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)C=O.OO.S(=O)(=O)(O)[OH:15]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([OH:15])[CH:9]=1

Participants

5

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-2 methoxybenzaldehyde (32.25 g, 0.15 mol) in methanol (300 ml) was added hydrogen peroxide (38 ml of 30% aqueous solution, 0.34 mol) and concentrated sulfuric acid (7 ml, 0.13 mol). The resulting solution was heated at 70° C. for 3 hr. and allowed to cool to room temperature. Stirring was continued for 60 hr. and the reaction mixture was concentrated under reduce pressure. The residue was partitioned between ether and water and the organic extract was washed with slightly acidic water (three times) and dried (magnesium sulfate). The solvent was removed in vacuo to provide an orange solid (30.6 g) which was used without further purification.

Workup

  1. temperatureto cool to room temperature
  2. concentrationand the reaction mixture was concentrated
  3. customThe residue was partitioned between ether and water
  4. extractionthe organic extract
  5. washwas washed with slightly acidic water (three times)
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c13dc61dcae24864898c6a4755ae1949
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

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