Chlorobenzene → 2,4,6-Trimethylbenzoic acid

HRID 903658Notes

Reaction equation

HRID 903658 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

6

Reactant 3

HCID 7964ChlorobenzeneHCID 7967CyclohexanoneHCID 102542,4,6-Trimethylbenzaldehyde

Product 1

HCID 101942,4,6-Trimethylbenzoic acidYield 55%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 176Acetic AcidSolvent

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 ws 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

  1. customTo a flask equipped with a stirrer, condenser and an oxygen inlet
  2. customOxygen ws bubbled in slowly while the solution
  3. temperatureThe reaction temperature was raised to 50°
  4. waitthe oxidation was continued for an additional 4 hr
  5. temperatureThe flask was cooled to 0°
  6. customthe reaction product was removed by filtration
  7. washwashed with petroleum ether

Sources & evidence

ORD record
ord-b1b1bb3978fe4a1a8fef59457aca4381
Source dataset
uspto-grants-1980_10
Patent number
US04228302

Reaction notes

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