Hydrochloric Acid → 2,5-Dimethyl-4-benzoquinone

HRID 1658848Notes

Reaction equation

HRID 1658848 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].CN1CCCCC1.[OH-:17].[Na+].Cl>C(Cl)(Cl)Cl>[CH3:8][C:5]1[C:6](=[O:17])[CH:7]=[C:2]([CH3:1])[C:3](=[O:9])[CH:4]=1

Participants

6

Procedure

12.2 g of 2,5-dimethylphenol (0.1 mole), 1.98 g of cobalt di-(3-methylsalcylal)-3,3'-diimino-di-n-propylamine (0.0005 mole) and 0.5 g of N-methylpiperidine were dissolved in 200 ml of chloroform and then air was bubbled through the resulting solution at 15°C for 10 hours during which time the reaction was completed. After completion of the reaction, the reaction mixture was rendered basic by adding a 2% aqueous solution of sodium hydroxide to decompose peroxides present in the mixture followed by addition of dilute hydrochloric acid to render the solution acidic. The resulting solution was extracted with ether which was then distilled off to obtain 12.1 g of 2,5-dimethyl-parabenzoquinone (0.09 mole).

Workup

  1. customair was bubbled through the resulting solution at 15°C for 10 hours during which time the reaction
  2. customAfter completion of the reaction
  3. extractionThe resulting solution was extracted with ether which
  4. distillationwas then distilled off

Sources & evidence

ORD record
ord-a0b58d17e72048ee9eaf4d290ae7b560
Source dataset
uspto-grants-1976_06
Patent number
US03966776

Reaction notes

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