Oxygen → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

HRID 1658849Notes

Reaction equation

HRID 1658849 reaction equation
CN(C)C.[O:5]=O.[CH3:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=1[OH:16]>C(Cl)(Cl)Cl>[CH3:15][C:11]1[C:12](=[O:5])[C:13]([CH3:14])=[C:8]([CH3:7])[C:9](=[O:16])[CH:10]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 1146TrimethylamineHCID 127692,3,5-Trimethylphenol

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

0.4 g of cobalt di-(5-methylsalcylal)-3,3'-diimino-di-n-propylamine (0.0001 mole) was dissolved in chloroform. To this was added 0.2 ml of an aqueous solution of 30% trimethylamine (0.0001 mole), which had been dissolved in 20 ml of chloroform, followed by the introduction of oxygen thereinto, but very little oxygen was absorbed. Upon adding a solution of 1.36 g of 2,3,5-trimethylphenol (0.01 mole) in 200 ml of chloroform to the above solution, the absorption of oxygen started, and in 5 hours the theoretical amount of oxygen was absorbed (224 ml). After the reaction was completed, the chloroform was distilled off and the residue was subjected to steam-distillation. The distillate was extracted with ether and the ether was then distilled off to give 1.5 g of pseudocumoquinone, (0.01 mole), that is, the yield was quantitative.

Workup

  1. customvery little oxygen was absorbed
  2. customthe absorption of oxygen
  3. customin 5 hours the theoretical amount of oxygen was absorbed (224 ml)
  4. distillationthe chloroform was distilled off
  5. distillationthe residue was subjected to steam-distillation
  6. extractionThe distillate was extracted with ether
  7. distillationthe ether was then distilled off

Sources & evidence

ORD record
ord-94eee985b75c4545bb7f885204aad47b
Source dataset
uspto-grants-1976_06
Patent number
US03966776

Reaction notes

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