Cyclohexanone → 2,4,6-Trimethylbenzoic acid

HRID 903661Notes

Reaction equation

HRID 903661 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(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[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 7187Benzoyl PeroxideCatalyst

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 benzoyl peroxide. Oxygen was bubbled in at fast rate while the stirred solution was maintained at 85°. After 24 hour an additional 50 mg of benzoyl peroxide was added and the reaction was continued at 90° for an additional 5 hr. After 29 hr total time the solution was mixed with 150 mL of water and 150 mL of methylene chloride; 20% aqueous potassium hydroxide was added dropwise until a pH of 8 was reached. The aqueous layer was separated and acidified with concentrated hydrochloric acid, after which the precipitated product was collected, washed with water and air dried to give 9.74 g (88% yield) of white mesitoic acid: mp 153°-155°.

Workup

  1. customTo a flask equipped with a stirrer, oxygen inlet and condenser
  2. customOxygen was bubbled in at fast rate while the stirred solution
  3. temperaturewas maintained at 85°
  4. additionAfter 24 hour an additional 50 mg of benzoyl peroxide was added
  5. additionAfter 29 hr total time the solution was mixed with 150 mL of water and 150 mL of methylene chloride
  6. addition20% aqueous potassium hydroxide was added dropwise until a pH of 8
  7. customThe aqueous layer was separated
  8. customafter which the precipitated product was collected
  9. washwashed with water and air
  10. customdried

Sources & evidence

ORD record
ord-3459dc57e81246659a3826336154e224
Source dataset
uspto-grants-1980_10
Patent number
US04228302

Reaction notes

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