Ethanol → Ethyl 2,4-dichloro-5-fluorobenzoylacetate

HRID 64977

반응식

HRID 64977 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]([CH:12]=[C:13](Cl)Cl)=[O:11].[Na].S(=O)(=O)(O)[OH:18].[CH2:22]([OH:24])[CH3:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]([CH2:12][C:13]([O:24][CH2:22][CH3:23])=[O:18])=[O:11]

참가 물질

6

반응물 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5360545SodiumHCID 136450062,2-Dichlorovinyl 2,4-dichloro-5-fluorophenyl ketone

생성물 1

HCID 2774350Ethyl 2,4-dichloro-5-fluorobenzoylacetate수율 79.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

28.8 g (0.1 mole) of 2,2-dichlorovinyl 2,4-dichloro-5-fluoro-phenyl ketone are added in portions to a solution of 4.6 g of sodium in 80 ml of absolute ethanol at 0°-5° C., while cooling (ice/methanol) and stirring. When the exothermic reaction has subsided, the mixture is stirred at room temperature for a further 30 minutes, the solvent is stripped off in vacuo and the residue is taken up in 100 ml of methylene chloride. The mixture is shaken thoroughly with 100 ml of 2N sulphuric acid, the methylene chloride solution is separated off in a separating funnel and the aqueous phase is extracted another three times with 50 ml of methylene chloride each time. The combined methylene chloride solutions are washed with 100 ml of saturated sodium chloride solution and dried over sodium sulphate. The solvent is then distilled off in vacuo. The brown oily residue crystallizes on standing. Distillation under a fine vacuum gives 22.3 g (79.9%) of ethyl 2,4-dichloro-5-fluoro-benzoylacetate of boiling point 125°-126° C./0.16 mbar. Colorless crystals of melting point 44°-45° C.

후처리

  1. customWhen the exothermic reaction
  2. stirringthe mixture is stirred at room temperature for a further 30 minutes
  3. customthe methylene chloride solution is separated off in a separating funnel
  4. extractionthe aqueous phase is extracted another three times with 50 ml of methylene chloride each time
  5. washThe combined methylene chloride solutions are washed with 100 ml of saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. distillationThe solvent is then distilled off in vacuo
  8. customThe brown oily residue crystallizes
  9. distillationDistillation under a fine vacuum

출처 및 근거

ORD 기록
ord-87085a22141c4b4fb585099106d734ca
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04611080

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