Acetic Acid → 4-tert-Butylbenzoic acid

HRID 1182336Notes

Reaction equation

HRID 1182336 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:12]N1C(=O)N(O)C(=O)N(O)C1=O.[C:24]([OH:27])(=[O:26])[CH3:25].O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[C:1]([C:5]1[CH:10]=[CH:9][C:25]([C:24]([OH:27])=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 73904-tert-ButyltolueneHCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 2

HCID 74034-tert-Butylbenzoic acidHCID 703244-tert-Butylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.445 g of 4-t-butyltoluene, 0.016 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to 4-t-butyltoluene), 5 g of acetic acid and 0.004 g of cobalt(II) acetate.4 H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 2 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield 4-t-butylbenzoic acid and 4-t-butylbenzaldehyde in 97% and 1% yields, respectively, at 100% conversion of 4-t-butyltoluene.

Sources & evidence

ORD record
ord-369989cb810d4f3fb977be47e56961ea
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

Loading…