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

HRID 944

Reaction equation

HRID 944 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-8f5c842320a64990ae9a69c2e501100d
Source dataset
uspto-grants-1998_03
Patent number
US05723470

Linked notes

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