Nitric Acid → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

HRID 1580243Notes

Reaction equation

HRID 1580243 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](Cl)[CH:5]=[C:4]([CH3:10])[C:3]=1[OH:11].[N+]([O-])(O)=[O:13]>C(O)(=O)C>[CH3:1][C:2]1[C:3](=[O:11])[C:4]([CH3:10])=[CH:5][C:6](=[O:13])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2621024-Chloro-2,3,6-trimethylphenol

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Yield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

17.0 g (0.1 mole) of 2,3,6-trimethyl-4-chlorophenol obtained in Example 1 (A) was dissolved in 100 g of acetic acid, and 10 g of concentrated nitric acid was added dropwise thereto in 30 minutes under stirring. The reaction proceeded immediately. After stirring for another 30 minutes, the reaction solution was subjected to steam distillation. The same treatment as in Example 1 was conducted to obtain 13.8 g of 2,3,6-trimethyl-p-benzoquinone (92.0 percent in yield).

Workup

  1. stirringAfter stirring for another 30 minutes
  2. distillationthe reaction solution was subjected to steam distillation

Sources & evidence

ORD record
ord-e8552504f7cb46069c418e3f30487d62
Source dataset
uspto-grants-1976_01
Patent number
US03932475

Reaction notes

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