Cyclohexanone → 2,3,4,6-Tetramethylbenzoic acid

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Reaction Steps

To a flask equipped with an oxygen inlet, stirrer and condenser were added 2,3,4,6-tetramethylbenzaldehyde (8.10 g, 50 mmol), 20 mL (0.194 mol) of cyclohexanone and 4 mg of cobalt (II) acetate dissolved in several drops of acetic acid. Oxygen was bubbled in while the solution was rapidly stirred. After 21/2 hr at room temperature and 4 hr at 50° the solution was poured into a separatory funnel and extracted with 100 mL, then 50 mL, of 3% aqueous sodium bicarbonate solution. The combined aqueous extracts were rinsed with 50 mL of cyclohexane, then acidified to a pH of 2 with concentrated hydrochloric acid and the precipitated product was collected by filtration, washed with water and air dried. A total of 5.2 g (58% yield) of fluffy white 2,3,4,6-tetramethylbenzoic acid was obtained: mp 164°-167°.

Provenance & Evidence