Oxygen → 2,4,6-Trimethylphenol

HRID 1658977Notes

Reaction equation

HRID 1658977 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[OH-:11].[Na+].O=O>O>[OH:11][C:6]1([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3](=[O:10])[C:2]([CH3:1])=[CH:7]1.[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10]

Participants

6

Reactant 3

HCID 977OxygenHCID 106982,4,6-TrimethylphenolHCID 14798Sodium Hydroxide

Product 2

HCID 106982,4,6-TrimethylphenolHCID 3272344-Hydroxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45 Parts of 2,4,6-trimethylphenol, 10 parts of sodium hydroxide, and 150 parts of water were fed to a stainless steel autoclave equipped with a gas-introducing pipe, temperature recorder and stirrer, and 100 Kg/cm2G oxygen pressure was applied. The reaction was conducted at 30°C. for 120 minutes, during which the pressure was reduced to 83 Kg/cm2G. The reaction product was recovered and extracted 2 times with 150 g of benzene with shaking. Analyses of benzene parts and water parts yielded 31.130 parts of 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadiene-1-one and 3.866 parts of unreacted 2,4,6-trimethylphenol from the benzene parts. 0.705 Parts of 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadiene-1-one and 0.090 parts of unreacted 2,4,6-trimethylphenol were also yielded from the water parts. Analyses of the results proved 91.2 % of conversion and 69.4 % of selectivity. Expelling the benzene out of said benzene solution and concentrating the benzene, 34 parts of oily product was obtained. The oily product was analyzed to be composed of 92.2 % of 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadiene-1-one and 9.6 % of 2,4,6-trimethylphenol.

Workup

  1. customThe reaction product was recovered
  2. extractionextracted 2 times with 150 g of benzene

Sources & evidence

ORD record
ord-e7c971c42705431c8dea4bf34ebdd609
Source dataset
uspto-grants-1976_06
Patent number
US03966818

Reaction notes

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