Acetic Anhydride → Phthalic Anhydride

HRID 971453Notes

Reaction equation

HRID 971453 reaction equation
[NH-][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:11]([OH:13])=[O:12].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>>[C:5]1(=[O:7])[O:13][C:11](=[O:12])[C:3]2=[CH:2][CH:10]=[CH:9][CH:8]=[C:4]12

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 178514214HCID 178514214, compound

Product 1

HCID 6811Phthalic Anhydride

Conditions

Temperature
80 °C

Procedure

13.8 g (0.04 mol) of this amidylphthalic acid are mixed with 1.4 g of anhydrous sodium acetate and 25 ml of acetic anhydride and the mixture is heated to 80° C. for 30 minutes, whilst stirring. The resulting reaction solution is evaporated to dryness, the residue is extracted with 60 ml of hot benzene and the benzene solution is filtered using animal charcoal. After evaporating the benzene, the residue is dried for 24 hours at 60° C./0.05 mm Hg. 9.95 g (80% theory) of crystalline 3-(bicyclo[1.2.2]hept-5-ene-2,3-dicarboxylic acid imidyl)-phthalic anhydride are obtained; melting point 178°-180° C.

Workup

  1. customThe resulting reaction solution
  2. customis evaporated to dryness
  3. extractionthe residue is extracted with 60 ml of hot benzene
  4. filtrationthe benzene solution is filtered
  5. customAfter evaporating the benzene
  6. customthe residue is dried for 24 hours at 60° C./0.05 mm Hg

Sources & evidence

ORD record
ord-011c2e89705146d38a1631c794a9a5c0
Source dataset
uspto-grants-1979_07
Patent number
US04160081

Reaction notes

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