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

HRID 1658847Notes

Reaction equation

HRID 1658847 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[OH:17].[O:18]=O>C(Cl)(Cl)Cl>[CH3:16][C:12]1[C:13](=[O:18])[C:14]([CH3:15])=[C:9]([CH3:8])[C:10](=[O:17])[CH:11]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 8471TriethylamineHCID 127692,3,5-Trimethylphenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

3.96 g of cobalt di-(salcylal)-3,3'-diimino -di-n-propylamine (0.1 mole) and 1.01 g of triethylamine (0.01 mole) were dissolved in 100 ml of chloroform and oxygen gas (100 ml/min) was then bubbled into the resulting solution for 5 seconds at a temperature of 10°C to form an oxygen complex. To this was added a solution of 13.6 g of 2,3,5-trimethylphenol (0.1 mole) in 100 ml of chloroform in three portions and oxygen gas (250 ml/min) was again introduced into the solution for a period of 8 hours to complete the reaction. After completion of the reaction, chloroform was distilled off and the residue was steam distilled by introducing steam thereinto. The distillate was extracted with ether and the ether was then distilled off to give 15.0 g of pseudocumoquinone (0.1 mole) having a melting point of 32°C, that is, the yield was quantitative.

Workup

  1. customoxygen gas (100 ml/min) was then bubbled into the resulting solution for 5 seconds at a temperature of 10°C
  2. customto form an oxygen complex
  3. additionwas again introduced into the solution for a period of 8 hours
  4. customthe reaction
  5. distillationwas distilled off
  6. distillationdistilled
  7. additionby introducing steam
  8. extractionThe distillate was extracted with ether
  9. distillationthe ether was then distilled off

Sources & evidence

ORD record
ord-5079b9710b50423982679447e0f1e44c
Source dataset
uspto-grants-1976_06
Patent number
US03966776

Reaction notes

Loading…