Oxygen → 2,5-Cyclohexadien-1-one, 4-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-2,6-dimethyl-

HRID 1657681Notes

Reaction equation

HRID 1657681 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11].O=O>ClCCCl.C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[CH3:3][C:4]1[C:5](=[O:1])[C:6]([CH3:10])=[CH:7][C:8](=[C:8]2[CH:7]=[C:6]([CH3:10])[C:5](=[O:11])[C:4]([CH3:3])=[CH:9]2)[CH:9]=1

Participants

6

Reactant 3

HCID 977OxygenHCID 113352,6-DimethylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 786212,5-Cyclohexadien-1-one, 4-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-2,6-dimethyl-

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
30 °C

Procedure

The reaction was carried out in the same manner as in Comparative Example 1 without employing sodium hydroxide. More specifically, after 122 gm (1.0 mole) of 2,6-dimethylphenol had been dissolved in 2200 gm of 1,2-dichloroethane and 32.5 gm (0.1 mole) of "Salcomine" had been added to the solution, oxygen was passed into the mixture at 30°C. The temperature of the reaction system was raised gradually, but it was maintained at 30°C by cooling. During the above procedure there was formed 3,3',5,5'-tetramethyldiphenoquinone. After 5 hours had passed, the reaction mixture was filtered, and the filtrate was poured into 20 liters of methanol containing 2 liters of hydrochloric acid but precipitation of a polymer was not observed. The amount of diphenoquinone obtained was 12.3 gm, the yield being 10.1%.

Workup

  1. customwas passed into the mixture at 30°C
  2. temperatureThe temperature of the reaction system was raised gradually
  3. temperatureby cooling

Sources & evidence

ORD record
ord-7cee3e5a5d38451c883c6405ba9136d0
Source dataset
uspto-grants-1976_06
Patent number
US03962181

Reaction notes

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