Acetic Acid → 4-Bromobenzoic acid

HRID 364689Notes

Reaction equation

HRID 364689 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6]C(C)=[CH:4][CH:3]=1.[C:9]([OH:12])(=[O:11])[CH3:10]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Br-].[Na+].C([O-])(=O)C.[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:10]([C:9]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 78054-Bromotoluene

Product 1

HCID 114644-Bromobenzoic acidYield 82.9%

Reagents, catalysts & solvents 4

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 253881Sodium BromideCatalystHCID 517045Sodium AcetateCatalystHCID 962WaterSolvent

Procedure

The test described in Example 1 was repeated using 300 g of p-bromotoluene, 700 g of acetic acid, 50 g of water, 6 g of cobalt acetate tetrahydrate, 5 g of sodium bromide and 5 g of sodium acetate. In a reaction time of 170 minutes, 292.4 g of p-bromobenzoic acid was obtained (80% of the theory).

Sources & evidence

ORD record
ord-4534a2ad379740259994ae98f8721f73
Source dataset
uspto-grants-1986_08
Patent number
US04605757

Reaction notes

Loading…