Acetic Anhydride → Phthalic Anhydride

HRID 1576064Notes

Reaction equation

HRID 1576064 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% of 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-174290caf8c14dfa9a2d1a69f793f561
Source dataset
uspto-grants-1976_09
Patent number
US03979393

Reaction notes

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