Cyclohexanone → 2,4,6-Trimethylbenzoic acid

HRID 903659Notes

Reaction equation

HRID 903659 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].C1(=[O:18])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:18])=[O:10]

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 102542,4,6-Trimethylbenzaldehyde

Product 1

HCID 101942,4,6-Trimethylbenzoic acid

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 (14.8 g, 0.10 mol), 30 mL (0.29 mol) of cyclohexanone and 10 mg of cobalt (II) acetate dissolved in 1 mL of acetic acid. Oxygen was bubbled in while the solution was stirred rapidly. Within an hour the temperature had risen to 70°, then declined rapidly. After 3 hr the solution was mixed with 75 ml of methylene chloride and 100 ml of water. Aqueous potassium hydroxide (40%) was added dropwise until the pH reached 7.5. The aqueous layer was separated and rinsed first with 50 mL of methylene chloride, then with 50 mL of petroleum ether. After acidification with concentrated hydrochloric acid, the white crystalline product was collected by filtration, washed with water and air dried: 12.54 g (77%) of mesitoic acid, mp 154°-156°.

Workup

  1. customTo a flask equipped with a stirrer, condenser and an oxygen inlet
  2. customOxygen was bubbled in while the solution
  3. waitWithin an hour the temperature had risen to 70°
  4. additionAfter 3 hr the solution was mixed with 75 ml of methylene chloride and 100 ml of water
  5. additionAqueous potassium hydroxide (40%) was added dropwise until the pH
  6. customThe aqueous layer was separated
  7. washrinsed first with 50 mL of methylene chloride
  8. filtrationAfter acidification with concentrated hydrochloric acid, the white crystalline product was collected by filtration
  9. washwashed with water and air
  10. customdried

Sources & evidence

ORD record
ord-f94776461e134b9aa0b5b34d444cc622
Source dataset
uspto-grants-1980_10
Patent number
US04228302

Reaction notes

Loading…