Chlorobenzene → 2,4,6-Trimethylbenzoic acid
Reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:9]=[O:10].ClC1C=CC=CC=1.C1(=[O:25])CCCCC1>C(O)(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:3]1([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:11])[C:2]=1[C:9]([OH:25])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a flask equipped with a stirrer, condenser and an oxygen inlet were added mesitaldehyde (20.0 g, 0.135 mol), 15 mL of chlorobenzene, 15 mL (0.145 mol) of cyclohexanone and 10 mg of cobalt (II) acetate dissolved in 1 mL of acetic acid. Oxygen was bubbled in slowly while the solution was stirred overnight. The reaction temperature was raised to 50° and the oxidation was continued for an additional 4 hr. The flask was cooled to 0° and the reaction product was removed by filtration and washed with petroleum ether. A total of 12.0 g (55% yield) of crystalline mesitoic acid was obtained. Additional mesitoic acid (2.4 g) was obtained from the filtrate by evaporation, dissolution of the residue in ether, extraction of the ether solution with aqueous sodium bicarbonate and acidification of the aqueous extract. The total yield of product was 65%. The identity of the product was confirmed by its nmr spectrum (CDCl3).
Workup
- customTo a flask equipped with a stirrer, condenser and an oxygen inlet
- customOxygen was bubbled in slowly while the solution
- temperatureThe reaction temperature was raised to 50°
- waitthe oxidation was continued for an additional 4 hr
- temperatureThe flask was cooled to 0°
- customthe reaction product was removed by filtration
- washwashed with petroleum ether
Sources & evidence
- ORD record
- ord-f01003aed69c47eb9ee42f33fe59b066
- Source dataset
- uspto-grants-1980_03
- Patent number
- US04195040
Reaction notes
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