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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence