Water → 3,4-Dichloro-3,4,4-trifluorobutanoic acid

HRID 439670

Reaction equation

HRID 439670 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(=O)=O.CC(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]

Participants

8

Reactant 6

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

Product 1

HCID 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 add (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-25e552637f484c7c974664d26f02bba0
Source dataset
uspto-grants-1996_05
Patent number
US05514717

Linked notes

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