Cyclohexanone → 2,3,4,6-Tetramethylbenzoic acid
Reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([CH3:11])[CH:7]=[C:6]([CH3:12])[C:3]=1[CH:4]=[O:5].C1(=[O:19])CCCCC1>C(O)(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([CH3:11])[CH:7]=[C:6]([CH3:12])[C:3]=1[C:4]([OH:19])=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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°.
Workup
- customTo a flask equipped with an oxygen inlet, stirrer and condenser
- customOxygen was bubbled in while the solution
- additionAfter 21/2 hr at room temperature and 4 hr at 50° the solution was poured into a separatory funnel
- extractionextracted with 100 mL
- washThe combined aqueous extracts were rinsed with 50 mL of cyclohexane
- filtrationthe precipitated product was collected by filtration
- washwashed with water and air
- customdried
Sources & evidence
- ORD record
- ord-dab9bfc618d544449d46b7c5022a3c8a
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04228302
Reaction notes
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