Hydrogen Peroxide → 2,6-Dimethylhydroquinone

HRID 1678935Notes

Reaction equation

HRID 1678935 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.OO.S(=O)(=O)(O)[OH:13].CC1C=C(C)C=C(O)C=1O>CC(C)CC(=O)C>[CH3:8][C:6]1[CH:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[C:7]=1[OH:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 79483,5-DimethylphenolHCID 177373,5-Dimethylbenzene-1,2-diol

Product 1

HCID 695602,6-Dimethylhydroquinone

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

In a vessel used in Example 52 were placed 100 g. (819 m. moles) of 3,5-dimethylphenol, 3.61 g. (36.1 m. moles) of 4-methyl-2-pentanone, 2.88 g. (50.8 m. moles) of 60 percent hydrogen peroxide and 0.01 g. of sulfuric acid, and the mixture was reacted at 110° C. for 20 minutes in the same manner as in Example 52. The reaction mixture was analyzed with gas chromatography. As products, 3.19 g. (23.1 m. moles) of 3,5-dimethylcatechol and 2.24 g. (16.2 m. moles) of 2,6-dimethylhydroquinone were obtained. The yield of dihydric alkylphenols was 77.4 percent.

Workup

  1. customIn a vessel used in Example 52

Sources & evidence

ORD record
ord-f81d1c09785942a2be0cbd332d636dfb
Source dataset
uspto-grants-1978_03
Patent number
US04078006

Reaction notes

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