Phenol → Phenol

HRID 1580538Notes

Reaction equation

HRID 1580538 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C(S(O)(=O)=[O:15])=CC=CC=1>[Cu].CO>[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:4]1(=[O:15])[CH:5]=[CH:6][C:1](=[O:7])[CH:2]=[CH:3]1

Participants

6

Reactant 2

HCID 996PhenolHCID 69252-Methylbenzenesulfonic acid

Product 2

HCID 996PhenolYield 1%HCID 4650Quinone

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Twenty milligrams of the inactive copper salt complex obtained from Example 1, 100 milligrams of phenol and 1 gram of methanol were dissolved in a 1/2 ounce bottle. Twenty micrograms of toluene sulfonic acid were added and solution was effected under steam heat at 100° C. One-half of the insoluble complex appeared to go into solution. One hundred microliters of the solution were charged into a micro reactor and reacted under the same conditions as described in Example 2. Samples were taken at 30 and 60 minutes. After 30 minutes of oxidation, a conversion of less than 1 percent phenol to benzoquinone was obtained. After 60 minutes reaction time, 4.74 percent conversion of phenol to benzoquinone was obtained.

Workup

  1. customreacted under the same conditions
  2. customwere taken at 30 and 60 minutes

Sources & evidence

ORD record
ord-dbc492455ae54330a5736547eee667cd
Source dataset
uspto-grants-1976_01
Patent number
US03933681

Reaction notes

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