Hydrogen Peroxide → 3-(Benzyloxy)-4-methoxyphenol

HRID 2268117Notes

Reaction equation

HRID 2268117 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.S(=O)(=O)(O)[OH:22]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 806713-Benzyloxy-4-methoxybenzaldehyde

Product 1

HCID 135310983-(Benzyloxy)-4-methoxyphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 3-benzyloxy-4-methoxybenzaldehyde (10 g) in MeOH (100 mL) was added hydrogen peroxide (5.5 mL of 30% aqueous) dropwise. After having been warmed to RT, concentrated sulfuric acid (1 mL) was added and the resulting solution was allowed to stir for 1.5 h. The reaction mixture was partitioned between ethyl ether/saturated aqueous sodium bicarbonate, another organic layer was dried over sodium sulfate and concentrated in vacuo to afford an oil. Flash chromatography (20% ethyl acetate/hexanes) afforded 3-benzyloxy-4-methoxyphenol (5.8 g).

Workup

  1. temperatureAfter having been warmed to RT
  2. customThe reaction mixture was partitioned between ethyl ether/saturated aqueous sodium bicarbonate
  3. dry with materialanother organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford an oil

Sources & evidence

ORD record
ord-3607f27afb7b4664b7a7e579ce827f58
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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