3,5-Dichlorobenzene-1,2-dicarboxylic acid → 1,3-Isobenzofurandione, 4,6-dichloro-

HRID 1654276Notes

Reaction equation

HRID 1654276 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:12]([OH:14])=[O:13]>O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:4]2[C:5]([O:14][C:12](=[O:13])[C:3]=12)=[O:7]

Participants

3

Reactant 1

HCID 144187813,5-Dichlorobenzene-1,2-dicarboxylic acid

Product 1

HCID 1040341,3-Isobenzofurandione, 4,6-dichloro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-Dichlorophthalic acid (3.36 g, preparation given in Example 1 of U.S. Pat. No. 5,086,188) was refluxed with 10 mL of xylenes while the water generated from the cyclization was collected in a Barrett trap. After refluxing for 5 hours the reaction was cooled, and the xylenes were removed under vacuum. The resultant solids were dried overnight in a vacuum desiccator to give 2.32 g of 3,5-dichlorophthalic anhydride, mp 90° to 94° C.

Workup

  1. customwas collected in a Barrett trap
  2. temperatureAfter refluxing for 5 hours the reaction
  3. temperaturewas cooled
  4. customthe xylenes were removed under vacuum
  5. customThe resultant solids were dried overnight in a vacuum desiccator

Sources & evidence

ORD record
ord-0fc80541e9894187ab85966c7e2e1ab8
Source dataset
uspto-grants-1995_04
Patent number
US05405995

Reaction notes

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