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

HRID 2412311Notes

Reaction equation

C(O)(C)C.[O:5]([CH3:7])[Na].[CH3:8][C:9]1[C:14](C)=[CH:13][CH:12]=[C:11]([CH3:16])[C:10]=1[OH:17].C(OO)(C)(C)C>CO.O>[CH3:13][C:14]1[C:7](=[O:5])[CH:12]=[C:11]([CH3:16])[C:10](=[O:17])[C:9]=1[CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

10 g of HCL gas were passed into 400 ml of isopropanol at room temperature, 4 g (0.028 mole) of Cu2O were added to the resulting solution, the mixture was heated at 70° C. and 75 liters/hour of air were passed in for 4 hours. Thereafter, 24 ml of a 30% strength solution of NaOCH3 in CH3OH were added at room temperature (a sample has a pH of 4.2 after water had been added), followed by the addition of 28 g (0.2 mole) of 2,3,6-trimethylphenol, the mixture was heated at 40° C. and 18 g (0.2 mole) of tert.-butyl hydroperoxide were then added in the course of 2 hours. At the same time, 75 liters/hour of air were passed into the reaction mixture. After a reaction time of 12 hours, the mixture was worked up as described in Example 1 to give 22.54 g of 99.7% pure 2,3,5-trimethyl-p-benzoquinone. The yield was thus 76% of theory.

Workup

customwere passed in for 4 hours
additionhad been added),
temperaturethe mixture was heated at 40° C.
customAfter a reaction time of 12 hours

Sources & evidence

ORD record: ord-409cdd31e5cb46a28f4fee0e40307e93
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04491545

Reaction notes

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