Cyclohexanone → 2,4,6-Trimethylbenzoic acid

HRID 1701688Notes

Reaction equation

HRID 1701688 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>N(C(C)(C)C#N)=NC(C)(C)C#N>[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

4

Reactant 2

HCID 7967CyclohexanoneHCID 102542,4,6-Trimethylbenzaldehyde

Product 1

HCID 101942,4,6-Trimethylbenzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst

Procedure

To a flask equipped with a stirrer, oxygen inlet and condenser were added mesitaldehyde (10.0 g, 67.6 mmol), 25 mL (0.242 mol) of cyclohexanone and 100 mg of azobisisobutyronitrile. Oxygen was bubbled in while the solution was stirred and maintained at 60°. After 45 hr the solution was mixed with 250 mL of water and 250 mL of methylene chloride; 20% aqueous potassium hydroxide was added dropwise until a pH of 8-9 was reached. The aqueous layer was separated and acidified with concentrated hydrochloric acid, after which the white solid product was collected by filtration, washed with water and air dried: 9.76 g (88% yield) of mesitoic acid.

Workup

  1. customTo a flask equipped with a stirrer, oxygen inlet and condenser
  2. customOxygen was bubbled in while the solution
  3. temperaturemaintained at 60°
  4. additionAfter 45 hr the solution was mixed with 250 mL of water and 250 mL of methylene chloride
  5. addition20% aqueous potassium hydroxide was added dropwise until a pH of 8-9
  6. customThe aqueous layer was separated
  7. filtrationafter which the white solid product was collected by filtration
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-ae508ea9256f4ae38d43dafcb9a50fcd
Source dataset
uspto-grants-1980_03
Patent number
US04195040

Reaction notes

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