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

HRID 1580245Notes

Reaction equation

II.[CH3:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([CH3:11])[C:5]=1[OH:12].C(O)(=[O:15])C>>[CH3:3][C:4]1[C:5](=[O:12])[C:6]([CH3:11])=[CH:7][C:8](=[O:15])[C:9]=1[CH3:10]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 807Iodine

HCID 170162,3,6-Trimethylphenol

Product 1

HCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-Yield 94.7%

Procedure

Halogenation and subsequent oxidation were conducted in the same manner as in Example 8 except for adding 0.068 g of iodine to the acetic acid solution of 2,3,6-trimethylphenol upon chlorination. Thus, there was obtained 14.2 g (94.7 percent in yield) of 2,3,6-trimethyl-p-benzoquinone.

Sources & evidence

ORD record: ord-dd5360d83fdc4356965ebd91604158f1
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03932475

Reaction notes

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