Acetic Acid → 2,4,6-Trimethylbenzoic acid

HRID 903657Notes

Reaction equation

HRID 903657 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.C(O)(=[O:21])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:21])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7964ChlorobenzeneHCID 102542,4,6-Trimethylbenzaldehyde

Product 1

HCID 101942,4,6-Trimethylbenzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Procedure

To a flask equipped with a stirrer, condenser and oxygen inlet tube were added mesitaldehyde (14.8 g, 0.10 mol), 25 mL of chlorobenzene and a solution of 10 mg of cobalt (II) acetate in 1 mL of acetic acid. Oxygen was bubbled in while the solution was vigorously stirred. The reaction temperature rose to 88° in 20 min and then returned to room temperature after one hour. The reaction mixture was mixed with 60 mL of methylene chloride, and 100 mL of water was added. Aqueous potassium hydroxide (40%) was added dropwise until the pH reached 8. The aqueous layer was separated, washed successively with 50 mL of methylene chloride and 50 mL of petroleum ether, and acidified with concentrated hydrochloric acid to a pH of 2. The white solid product was collected by filtration, washed with water and air dried to give 9.82 g (60% yield) of mesitoic acid: mp 153.5°-155.5° C.

Workup

  1. customTo a flask equipped with a stirrer, condenser and oxygen inlet tube
  2. customOxygen was bubbled in while the solution
  3. waitreturned to room temperature after one hour
  4. additionThe reaction mixture was mixed with 60 mL of methylene chloride, and 100 mL of water
  5. additionwas added
  6. additionAqueous potassium hydroxide (40%) was added dropwise until the pH
  7. customThe aqueous layer was separated
  8. washwashed successively with 50 mL of methylene chloride and 50 mL of petroleum ether
  9. filtrationThe white solid product was collected by filtration
  10. washwashed with water and air
  11. customdried

Sources & evidence

ORD record
ord-615c935558a44baeb7875a2eb5bae1ea
Source dataset
uspto-grants-1980_10
Patent number
US04228302

Reaction notes

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