Hydrogen Peroxide → Catechol

HRID 846915Notes

Reaction equation

HRID 846915 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C(C)=[O:13])C(C)C.OO>>[C:1]1([C:6](=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:13])[OH:7].[C:1]1([CH:6]=[CH:5][C:4]([OH:13])=[CH:3][CH:2]=1)[OH:7]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 996PhenolHCID 7909Methyl Isobutyl Ketone

Product 2

HCID 289CatecholHCID 785Hydroquinone

Conditions

Temperature
100 °C

Procedure

In a 300 ml four-necked flask equipped with a stirrer, a condenser, and a thermometer were charged 65.8 g (0.7 mol) of phenol, 3.5 g (0.035 mol) of methyl isobutyl ketone, and 50 mg of each of the compounds shown in Table 1 below as a catalyst. The mixture was heated to 100° C., and 1.98 g (0.035 mol) of 60 wt % aqueous hydrogen peroxide was added thereto, followed by stirring for 30 minutes. The resulting reaction mixture was analyzed by gas chromatography to obtain yields of catechol and hydroquinone. The results obtained are shown in Table 1.

Workup

  1. customIn a 300 ml four-necked flask equipped with a stirrer, a condenser
  2. customThe resulting reaction mixture
  3. customto obtain

Sources & evidence

ORD record
ord-ff522065591d4b25b776461305f81ad5
Source dataset
uspto-grants-1992_08
Patent number
US05138104

Reaction notes

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