Acetic Acid → 4'-Acetoxy-biphenyl-4-carboxylic acid

HRID 981355Notes

Reaction equation

HRID 981355 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])C)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(O)(=[O:22])C>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:22])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 135310454-Acetoxy-4'-acetylbiphenyl

Product 1

HCID 6118364'-Acetoxy-biphenyl-4-carboxylic acidYield 51%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalyst

Procedure

500 ml of glacial acetic acid, 50.8 g of 4-acetoxy-4'-acetylbiphenyl, 0.8 g of cobalt(II) acetate and 12.0 g of manganese(II) acetate were refluxed in a 1 l double-walled flanged reactor equipped with an intensive stirrer and baffles, and the mixture was gassed with air via a valve in the base. After 4 hours, the mixture was cooled and the product was filtered off under suction, washed with water and dried. 26.1 g (51% yield) of 4-acetoxybiphenyl-4'-carboxylic acid having a purity of >98% (HPLC) were obtained.

Workup

  1. customequipped with an intensive stirrer
  2. custombaffles, and the mixture was gassed with air via a valve in the base
  3. temperaturethe mixture was cooled
  4. filtrationthe product was filtered off under suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-48f9f410703f474b865b196e22816bee
Source dataset
uspto-grants-1991_02
Patent number
US04990660

Reaction notes

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