Cyclohexanone → Pentamethylbenzoic acid

HRID 1701691Notes

Reaction equation

HRID 1701691 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([CH3:10])[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[CH3:13].C1(=[O:20])CCCCC1>C(O)(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH3:1][C:2]1[C:7]([C:8]([OH:20])=[O:9])=[C:6]([CH3:10])[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[CH3:13]

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 263712Pentamethylbenzaldehyde

Product 1

HCID 75236Pentamethylbenzoic acidYield 78.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6277Cobalt diacetateCatalyst

Procedure

To a flask equipped with a stirrer, oxygen inlet and condenser were added pentamethylbenzaldehyde (12.0 g, 68 mmol), 40 mL (0.387 mol) of cyclohexanone and 6 mg of cobalt (II) acetate dissolved in several drops of acetic acid. Oxygen was bubbled in while the solution was stirred rapidly and heated at 50° for 4 hours. The solution was mixed with 100 mL of cyclohexane and the mixture was extracted with 100 mL of 6% aqueous sodium bicarbonate solution. The aqueous layer was separated and the organic layer was washed with 50 mL of water. The combined aqueous layers were acidified with concentrated hydrochloric acid. The white crystalline solid product was collected by filtration, washed with water and air dried. A total of 10.3 g (78% yield) of pentamethylbenzoic acid was obtained: mp 202°-206°.

Workup

  1. customTo a flask equipped with a stirrer, oxygen inlet and condenser
  2. customOxygen was bubbled in while the solution
  3. temperatureheated at 50° for 4 hours
  4. additionThe solution was mixed with 100 mL of cyclohexane
  5. extractionthe mixture was extracted with 100 mL of 6% aqueous sodium bicarbonate solution
  6. customThe aqueous layer was separated
  7. washthe organic layer was washed with 50 mL of water
  8. filtrationThe white crystalline solid product was collected by filtration
  9. washwashed with water and air
  10. customdried

Sources & evidence

ORD record
ord-76bae2f78fb949b6ba0bfdd19b20aed5
Source dataset
uspto-grants-1980_03
Patent number
US04195040

Reaction notes

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