Oxygen → Phenol

HRID 1580537Notes

Reaction equation

HRID 1580537 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:9].O=O>CO>[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:4]1(=[O:9])[CH:5]=[CH:6][C:1](=[O:7])[CH:2]=[CH:3]1

Participants

6

Reactant 3

HCID 977OxygenHCID 996PhenolHCID 1118Sulfuric Acid

Product 2

HCID 996PhenolHCID 4650Quinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
100 °C

Procedure

Twenty milligrams of the inactive complex obtained as described in Example 1, 100 milligrams of phenol and one cubic centimeter of methanol were added to a 1/2 ounce bottle. The complex was insoluble in the methanol. Two microliter portions of concentrated sulfuric acid were added until 10 microliters were in the bottle. The insoluble complex went into solution with the methanol and acid when the mixture was heated with steam at 100° C. An oxidation was run with the solution formed by charging 100 microliters of said solution into a micro reactor, heating to 65° C., and charging 500 pounds per square inch gauge oxygen pressure. After oxidizing for 60 minutes, 29.6 percent conversion of phenol to benzoquinone was obtained.

Workup

  1. additionwere added to a 1/2 ounce bottle
  2. customformed
  3. temperatureheating to 65° C.

Sources & evidence

ORD record
ord-67a029e68255413bb479c5f7775dc2b7
Source dataset
uspto-grants-1976_01
Patent number
US03933681

Reaction notes

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