Sulfate Ion → 1,2,3,4-Tetrafluorobenzene

HRID 622255

Reaction equation

HRID 622255 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:4](C(O)=O)[C:3]=1C(O)=O.S([O-])([O-])(=O)=[O:18].[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:8]([F:13])=[C:9]([F:12])[C:10]=1[F:11].[F:1][C:2]1[CH:3]=[CH:4][C:8]([OH:18])=[C:9]([F:12])[C:10]=1[F:11]

Participants

6

Reactant 3

HCID 1117Sulfate IonHCID 14798Sodium HydroxideHCID 695443,4,5,6-Tetrafluorophthalic acid

Product 2

HCID 110841,2,3,4-TetrafluorobenzeneHCID 1231742,3,4-Trifluorophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

In an autoclave having an inner volume of 100 ml, 3.0 g (0.0126 mole) of 3,4,5,6-tetrafluorophthalic acid containing no sulfate ion, 0.5 g (0.0125 mole) of sodium hydroxide, and 50 g of water were placed and heated for reaction at 200° C. for 25 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with 150 ml of diisopropyl ether. By analyzing this extract by gas chromatography using a 2 m column packed with SE52 and kept at 50° C., the reaction was found to have produced 2.9 mole % of 1,2,3,4-tetrafluorobenzene, 89.1 mole % of trifluorophenol, and substantially no 2,3,4,5-tetrafluorobenzoic acid based on the 3,4,5,6-tetrafluorophthalic acid used as the starting material [pH 2.75 at 25° C. at the time of charging].

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionextracted with 150 ml of diisopropyl ether
  4. extractionthis extract by gas chromatography
  5. customkept at 50° C.

Sources & evidence

ORD record
ord-cd5760b79d004bedb9f906022f11db42
Source dataset
uspto-grants-1988_09
Patent number
US04769492

Linked notes

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