Water → 3,4,4-Trifluoro-3-butenoic acid

HRID 1940835Notes

Reaction equation

HRID 1940835 reaction equation
[Cl:1][C:2]([F:8])(Cl)[C:3]([F:6])([F:5])[Cl:4].[C:9](Cl)(Cl)=C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH:25]([O-:27])=[O:26].[Na+].O.[C:30](=[O:32])=[O:31].[CH3:33]C(C)=O>CN(C=O)C>[Cl:1][C:2]([F:8])([C:3]([Cl:4])([F:6])[F:5])[CH2:9][C:25]([OH:27])=[O:26].[F:8][C:2](=[C:3]([F:6])[F:5])[CH2:33][C:30]([OH:32])=[O:31]

Participants

9

Reactant 6

HCID 962WaterHCID 6366Vinylidene chlorideHCID 6428Cfc 113HCID 62648Ammonium PersulfateHCID 2723810Sodium FormateHCID 18522661Acetone cardice

Product 2

HCID 152391743,4,4-Trifluoro-3-butenoic acidHCID 218364853,4-Dichloro-3,4,4-trifluorobutanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,1,2-trichlorotrifluoroethane (X) (9.37 g, 50 mmol), vinylidene chloride (4.85 g, 50 mmol), ammonium persulfate (11.41 g, 50 mmol), sodium formate (3.4 g, 50 mmol) and water (1.8 g, 0.1 mol) in DMF (80 mL) was stirred (dry-ice/acetone condensor) at room temperature with air bubbling. After 30 min, an aliquot of the reaction mixture was acidified with dilute HCl, extracted with ether and analyzed by GC, which indicated the formation of two products. These products were identified by GC/MS (EI) as 4-chloro-3,4,4-trifluoro-2-butenoic acid and novel compound 3,4-dichloro-3,4,4-trifluorobutanoic acid (XI). The compound XI gives 3,4,4-trifluoro-3-butenoic acid (IV) upon reaction with zinc. Under the above reaction conditions, 1-chloro-1,2-dibromotrifluoroethane (VI) gave 3-chloro-4-bromo-3,4,4-trifluorobutanoic acid (VIII) as one of the products.

Workup

  1. custombubbling
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-12522daea5014e87a3c31bc0e200c2ef
Source dataset
uspto-grants-1997_12
Patent number
US05700840

Reaction notes

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