Acetic Acid → 3,4,5,6-Tetrafluorophthalic acid

HRID 622265Notes

Reaction equation

HRID 622265 reaction equation
C1(N2[C:11](=[O:12])[C:10]3=[C:13]([F:20])[C:14]([F:19])=[C:15]([F:18])[C:16]([F:17])=C3C2=O)CCCCC1.S(=O)(=O)(O)[OH:23].Cl.[C:28]([OH:31])(=[O:30])[CH3:29]>>[F:17][C:16]1[C:15]([F:18])=[C:14]([F:19])[C:13]([F:20])=[C:10]([C:11]([OH:23])=[O:12])[C:29]=1[C:28]([OH:31])=[O:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14274184HCID 14274184, compound

Product 1

HCID 695443,4,5,6-Tetrafluorophthalic acidYield 90%

Procedure

After mixing 50 g of the above dried N-cyclohexyl-tetrafluorophthalimide with 80 ml of 85% sulfuric acid, 80 ml of acetic acid was added to the mixture and it was reacted for 5 hours at 120° to 130° C. with stirring. After the reaction was completed, acetic acid was distilled off from the reaction mixture under a reduced pressure and the product was continuously extracted with toluene for 24 hours. When the toluene layer obtained was concentrated by distillation under a reduced pressure, crude crystals of yellow tetrafluorophthalic anhydride were precipitated. The concentrate was distilled under a reduced pressure (20 mmHg) at 150° C. and the crystals thus obtained were hydolyzed by adding 100 ml of an aqueous 6N hydrochloric acid solution. The hydrolyzed product was cooled and then extracted with ether to provide white crystals of tetrafluorophthalic acid (yield 90%).

Workup

  1. additionwas added to the mixture and it
  2. customwas reacted for 5 hours at 120° to 130° C.
  3. distillationacetic acid was distilled off from the reaction mixture under a reduced pressure
  4. extractionthe product was continuously extracted with toluene for 24 hours
  5. customWhen the toluene layer obtained
  6. concentrationwas concentrated by distillation under a reduced pressure
  7. customcrude crystals of yellow tetrafluorophthalic anhydride were precipitated
  8. distillationThe concentrate was distilled under a reduced pressure (20 mmHg) at 150° C.
  9. customthe crystals thus obtained
  10. temperatureThe hydrolyzed product was cooled
  11. extractionextracted with ether

Sources & evidence

ORD record
ord-7babdfdaecd3484597b6ed3cb1e91acc
Source dataset
uspto-grants-1988_09
Patent number
US04769493

Reaction notes

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