P-Toluic Acid → Methanone, (2,5-dimethylphenyl)(4-methylphenyl)-

Participants

Reaction Steps

A mixture of p-toluic acid (22.2 g, 0.163 mole), p-xylene (100 mL), and trifluoromethanesulfonic acid (5 mL; 0.056 mole) was heated at reflux for 21 hours in a 300 mL flask equipped with a Dean-Stark trap, after which time 3 mL of water had been collected in the trap. The progress of the reaction was measured by gas chromatography as well as by the amount of water collected. After 6 hours, 22% of starting material had been converted to 2,5,4'-trimethylbenzophenone. The mixture was extracted with water, with 5% aqueous sodium hydroxide solution, and again with water. Evaporation of the organic layer gave 24 g (0.11 mole) of 2,5,4'-trimethylbenzophenone, 66% of theory.

Provenance & Evidence