1,1'-Biphenyl-2,3',3,4'-tetracarboxylic acid → [4,5'-Biisobenzofuran]-1,1',3,3'-tetrone

HRID 1579074Notes

Reaction equation

HRID 1579074 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[C:15]([C:22]([OH:24])=O)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7](O)=[O:8])[C:2]=1[C:10]([OH:12])=[O:11]>C(OC(=O)C)(=O)C>[CH:5]1[CH:4]=[C:3]2[C:7]([O:11][C:10](=[O:12])[C:2]2=[C:1]([C:13]2[CH:18]=[CH:17][C:16]3[C:19]([O:21][C:22](=[O:24])[C:15]=3[CH:14]=2)=[O:20])[CH:6]=1)=[O:8]

Participants

3

Reactant 1

HCID 100195031,1'-Biphenyl-2,3',3,4'-tetracarboxylic acid

Product 1

HCID 3084646[4,5'-Biisobenzofuran]-1,1',3,3'-tetroneYield 80.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Acetic anhydride (400 ml.) was added to 116 g of 2,3,3',4'-biphenyltetracarboxylic acid having a melting point of 195° to 205°C., and the mixture was heated under reflux for 4 hours. The mixture was cooled, and allowed to stand. The crystals formed were filtered to provide 83 g (yield 80% of theoretical) of 2,3,3',4'-biphenyltetracarboxylic dianhydride having a melting point of 196° to 204°C. By further concentration of the filtrate, 17 g (16%) of 2,3,3',4'-biphenyltetracarboxylic dianhydride was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customThe crystals formed
  5. filtrationwere filtered

Sources & evidence

ORD record
ord-285ae75a1d1d4e968995c3ac26677b67
Source dataset
uspto-grants-1976_02
Patent number
US03940426

Reaction notes

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