Acetic Acid → 2,4,6-Trimethylbenzoic acid

Participants

Reaction Steps

To a flask equipped with a stirrer, condenser and oxygen inlet tube were added mesitaldehyde (14.8 g, 0.10 mol), 25 mL of chlorobenzene and a solution of 10 mg of cobalt (II) acetate in 1 mL of acetic acid. Oxygen was bubbled in while the solution was vigorously stirred. The reaction temperature rose to 88° in 20 min and then returned to room temperature after one hour. The reaction mixture was mixed with 60 mL of methylene chloride, and 100 mL of water was added. Aqueous potassium hydroxide (40%) was added dropwise until the pH reached 8. The aqueous layer was separated, washed successively with 50 mL of methylene chloride and 50 mL of petroleum ether, and acidified with concentrated hydrochloric acid to a pH of 2. The white solid product was collected by filtration, washed with water and air dried to give 9.82 g (60% yield) of mesitoic acid: mp 153.5°-155.5° C.

Provenance & Evidence