Acetic Anhydride → [4,5'-Biisobenzofuran]-1,1',3,3'-tetrone

HRID 31539Notes

Reaction equation

HRID 31539 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 2

HCID 7918Acetic AnhydrideHCID 100195031,1'-Biphenyl-2,3',3,4'-tetracarboxylic acid

Product 1

HCID 3084646[4,5'-Biisobenzofuran]-1,1',3,3'-tetroneYield 90.1%

Procedure

2,3,3′,4′-Biphenyltetracarboxylic acid (4) (33 gm, 100 mmol) was suspended in minimum amount of acetic anhydride and heated to reflux for 4 hours. The reaction mixture was cooled to room temperature. The corresponding dianhydride precipitated out and was collected and washed with ether to remove trace of acetic acid before drying under vacuum to afford 26.5 g (90%) of a-BPDA. Mp=195-196° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customThe corresponding dianhydride precipitated out
  4. customwas collected
  5. washwashed with ether
  6. customto remove trace of acetic acid
  7. custombefore drying under vacuum

Sources & evidence

ORD record
ord-fa3f9b4e43df40f3b8389354eea3dc8f
Source dataset
uspto-grants-2008_09
Patent number
US07425650B1

Reaction notes

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