4-Chlorobenzoic Acid → 4,4'-Oxydiphthalic anhydride

HRID 465739

Reaction equation

HRID 465739 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[C:13](=[O:16])([O-:15])[O-].[K+].[K+].Cl[C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1.[N+](C1C=CC=CC=1)([O-])=[O:30]>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:12]1[C:2]([O:30][C:28]2[CH:20]=[CH:21][C:22]3[C:13]([O:15][C:24](=[O:25])[C:23]=3[CH:27]=2)=[O:16])=[CH:3][C:4]2[C:9]([O:8][C:6](=[O:7])[C:5]=2[CH:11]=1)=[O:10]

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 7416Nitrobenzene2×HCID 11430Potassium Carbonate2×HCID 670444-Chlorophthalic anhydride

Product 1

HCID 745744,4'-Oxydiphthalic anhydride

Reagents, catalysts & solvents 1

HCID 2724163Tetraphenylphosphonium BromideCatalyst

Procedure

4-Chlorophthalic anhydride (30 g, 160 mmol), and nitrobenzene (Aldrich, 30 g, containing 500 ppm water) were heated to reflux. Dry potassium carbonate (1.32 g, 9.6 mmol) was added and the mixture heated for 30 minutes. Tetraphenyl phosphonium bromide (0.36 g, 0.9 mmol) and 4-chlorobenzoic acid (0.06 g, 0.4 mmol) were added followed by addition of potassium carbonate (11.4 g, 82.2 mmol). The reaction was heated for about 9 hours and then was diluted with nitrobenzene (30 g) and filtered. The 4,4'-oxydiphthalic anhydride was allowed to crystallize, was washed with solvent, and dried in an air circulating oven at 120° C. to give crude 4,4'-oxydiphthalic anhydride, 10.0 g.

Workup

  1. temperaturethe mixture heated for 30 minutes
  2. temperatureThe reaction was heated for about 9 hours
  3. filtrationfiltered
  4. customto crystallize
  5. washwas washed with solvent
  6. customdried in an air
  7. customat 120° C.

Sources & evidence

ORD record
ord-1f4db03b584f49bba0584bfca4a5bd52
Source dataset
uspto-grants-1992_10
Patent number
US05153335

Linked notes

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