Hydrogen Peroxide → Guaiacol

HRID 505978Notes

Reaction equation

HRID 505978 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:9]O>C(#N)C>[C:1]1([O:7][CH3:8])[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:9].[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 7519Anisole

Product 2

HCID 460GuaiacolHCID 90154-Methoxyphenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

In to a 150 ml round-bottomed double-necked flask containing anisole (0.05 mol, 5.4 g), 50% aq. hydrogen peroxide (0.25 mol, 17.0 g) in acetonitrile (50 ml) was added vanadyl tetraphenoxyphthalocyanine (2.5 mol %, 1.18 g). The reaction was continued with vigorous stirring at 65° C. for 8 h. The reaction mixture was then filtered through a Buckner funnel, passed through a short column of silica gel to remove the catalyst and concentrated under reduced pressure. The resulting residue was analyzed by high resolution GCMSD, EI, quadrapole mass analyzer, EM detector. The conversion of anisole was determined on the basis of the weight of the residue left after evaporation and yields of guaiacol and 4-methoxyphenol were determined by GC. Conversion of anisole was 18%. The yield of the mixture of guaiacol and 4-methoxyphenol was 17.5%.

Workup

  1. filtrationThe reaction mixture was then filtered through a Buckner funnel
  2. customto remove the catalyst
  3. concentrationconcentrated under reduced pressure
  4. waitleft
  5. customafter evaporation

Sources & evidence

ORD record
ord-7c569a774945444e80cf87bc3da748f5
Source dataset
uspto-grants-2010_08
Patent number
US07781622B2

Reaction notes

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