Acetylene → HCID 53816865, compound

HRID 1199753Notes

Reaction equation

HRID 1199753 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-:14].[Al+3].[Cl-].[Cl-].[CH:18]#[CH:19]>ClCCCl>[Cl:14][CH:18]=[CH:19][C:4]([C:3]1[CH:7]=[C:8]([F:13])[C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])=[O:5]

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53816865HCID 53816865, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

53.2 g of 2,3,4,5-tetrafluorobenzoyl chloride are added dropwise to a suspension of 36.5 g of anhydrous aluminum chloride in 100 ml of 1,2-dichloroethane at 0°-10° C., while cooling with ice and stirring. Acetylene is then passed in at 40°-50° C. for 7 hours and the mixture is poured onto ice. The phases are separated, subsequent extraction with methylene chloride is carried out and the extract is washed with water and dried with sodium sulphate. The solvent is distilled off in vacuo and the residue is distilled under a high vacuum. 49.2 g of 2,3,4,5-tetrafluorophenyl 2-chlorovinyl ketone pass over at 92°-105° C./1.5 mbar.

Workup

  1. temperaturewhile cooling with ice
  2. additionthe mixture is poured onto ice
  3. customThe phases are separated
  4. extractionsubsequent extraction with methylene chloride
  5. washthe extract is washed with water
  6. dry with materialdried with sodium sulphate
  7. distillationThe solvent is distilled off in vacuo
  8. distillationthe residue is distilled under a high vacuum
  9. customover at 92°-105° C./1.5 mbar

Sources & evidence

ORD record
ord-4c82c369844a419aa7609e0b592d25f5
Source dataset
uspto-grants-1990_02
Patent number
US04902795

Reaction notes

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