Hydrogen Peroxide → O-Cresol

HRID 434420Notes

Reaction equation

HRID 434420 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]([CH2:11][CH:12]([CH3:14])[CH3:13])=[O:10].OO>[Ti].O>[CH:3]1[C:4]([OH:10])=[CH:5][CH:6]=[C:1]([CH3:7])[CH:2]=1.[CH:11]1[C:9]([OH:10])=[CH:8][CH:1]=[CH:13][C:12]=1[CH3:14].[C:1]1([CH3:7])[C:6]([OH:10])=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 1140TolueneHCID 7909Methyl Isobutyl Ketone

Product 3

HCID 335O-CresolHCID 342M-CresolHCID 2879P-Cresol

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 500-ml flask is charged with 150 mls toluene, 100 mls methylisobutyl ketone, 40 mls of water and 20 g of titanium silicalite. To this slurry there are added 25 mls of 36% H2O2 while maintaining the temperature to 90° C. There are obtained 8.5 g of para cresol, 1.2 g of meta cresol, 1.9 g of ortho cresol, with a yield relative to H2O2 of 21%. 100 mls of such a solution are distilled and 4.2 g of cresols are obtained, with the following distribution of the isomers: 73.2% of para cresol, 10.34% of the meta isomer and 16.46% of the ortho isomer.

Sources & evidence

ORD record
ord-f9b7ae9274d44556aced368a1e61a324
Source dataset
uspto-grants-1983_08
Patent number
US04396783

Reaction notes

Loading…