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

HRID 1580241Notes

Reaction equation

HRID 1580241 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[N+]([O-])(O)=[O:12]>C(O)(=O)C.N([O-])=O.[Na+]>[CH3:9][C:4]1[C:3](=[O:10])[C:2]([CH3:1])=[C:7]([CH3:8])[C:6](=[O:12])[CH:5]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 170162,3,6-Trimethylphenol

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Yield 69.6%

Reagents, catalysts & solvents 2

HCID 23668193Sodium NitriteCatalystHCID 176Acetic AcidSolvent

Procedure

Also, in the process described in Japanese Pat. Publication No. 38063/70 (German Pat. OLS No. 1,814,652), 2,3,6-trimethylphenol is dissolved in acetic acid and oxidized with a dilute nitric acid using sodium nitrite as a catalyst to obtain trimethyl-p-benzoquinone in maximum yield of 69.6 percent. This process is simple and is considered to be a good one. However, the yield is a little low.

Sources & evidence

ORD record
ord-03c3211cbb2a4164b7eb9990a21a3510
Source dataset
uspto-grants-1976_01
Patent number
US03932475

Reaction notes

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