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

HRID 944노트

반응식

HRID 944 반응식
[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]

참가 물질

9

반응물 6

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

생성물 2

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. custombubbling
  2. extractionextracted with ether

출처 및 근거

ORD 기록
ord-8f5c842320a64990ae9a69c2e501100d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723470

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