Hydrochloric Acid → 2,3,6-Trimethylphenol

Participants

Reaction Conditions

Reaction Steps

55 g of hydrogen chloride were passed into 400 ml of isopropanol at room temperature, and 28 g (0.2 mole) of 2,5,6-trimethylcyclohex-2-en-1-one and 4 g (0.028 mole) of copper(I) oxide were added to the resulting solution. Thereafter, the reaction mixture was heated to 70° C., and 75 liters/hour of air were passed in for 3 hours, while stirring. Gas chromatographic analysis (2 m OV 17, 200° C.) then showed that 2,5,6-trimethylcyclohex-2-en-1-one was no longer present, and that 2,3,6-trimethylphenol as well as a little 4-chloro-2,3,6-trimethylphenol had beed formed. 243 ml of a 30% strength solution of sodium methylate in methanol were then run in at room temperature, and a sample of the reaction mixture, after water had been added to it, had a pH of 4.2. The mixture was then heated at 62° C., and 75 liters/hour of air, which had been fed in uninterrupted throughout the entire process, was passed into the mixture at 62° C. for a further 16 hours.

Provenance & Evidence