Acetic Acid → 4-tert-Butylbenzoic acid

HRID 746301Notes

Reaction equation

HRID 746301 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9]C(C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12]([OH:15])(=[O:14])[CH3:13]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Br-].[Na+]>[C:1]([C:5]1[CH:10]=[CH:9][C:13]([C:12]([OH:15])=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 73904-tert-Butyltoluene

Product 1

HCID 74034-tert-Butylbenzoic acidYield 86.4%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 253881Sodium BromideCatalyst

Procedure

Analogously to Example 1, 300 g of p-tert-butyltoluene (93.3% pure) was oxidized in the presence of 50 g of acetic acid, 3 g of cobalt acetate tetrahydrate and 1.5 g of sodium bromide at 25 bar and 115°-135° C. by passing air through it to produce a gas exhaust rate of 1.5 liters per minute. The oxygen absorption ended after a reaction period of 300 minutes; then 450 g of 74.5% acetic acid was added, the dilute reaction mixture was cooled with stirring to room temperature and filtered, and the crystallizate was washed with 450g of 70% acetic acid. 311.5 g of p-tert-butylbenzoic acid resulted, in the form of white crystals of a purity of 99.6 percent by weight as determined by gas chromatography, with a terephthalic acid content of 0.16%.

Workup

  1. customto produce a gas exhaust rate of 1.5 liters per minute
  2. customThe oxygen absorption
  3. customafter a reaction period of 300 minutes
  4. customthe dilute reaction mixture
  5. temperaturewas cooled
  6. filtrationfiltered
  7. washthe crystallizate was washed with 450g of 70% acetic acid

Sources & evidence

ORD record
ord-ce0a3f85e58a4eb1b31c67e6762ef737
Source dataset
uspto-grants-1986_07
Patent number
US04603220

Reaction notes

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