Thionyl Chloride → HCID 53824254, compound

HRID 1447440Notes

Reaction equation

HRID 1447440 reaction equation
[CH3:1][C:2]1([CH3:22])[CH:4]([CH:5]=[C:6]([Cl:18])[C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[CH:3]1[C:19](O)=[O:20].S(Cl)([Cl:25])=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:22])[CH:4]([CH:5]=[C:6]([Cl:18])[C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[CH:3]1[C:19]([Cl:25])=[O:20]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54111873HCID 54111873, compound

Product 1

HCID 53824254HCID 53824254, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

19.4 g (0.058 mol) of 2,2-dimethyl-3-(2-chloro-2-(4-trifluoromethoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid were dissolved in 150 ml of carbon tetrachloride, and 15 g of thionyl chloride were slowly added dropwise at 25° C., while stirring. The mixture was then heated to the reflux temperature for 4 hours. After this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation under 2 mm Hg at a bath temperature of 60° C. 19.4 g (95% of theory) of 2,2-dimethyl-3-(2-chloro-2-(4-trifluoromethoxy-phenyl)-vinyl)-cyclopropanecarboxylic acid chloride were obtained as an oily liquid.

Workup

  1. temperatureThe mixture was then heated to the reflux temperature for 4 hours
  2. distillationAfter this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum
  3. customLast residues of solvent were removed by brief incipient distillation under 2 mm Hg at a bath temperature of 60° C

Sources & evidence

ORD record
ord-b5cad4985a1047ef9689c1200a97a7c9
Source dataset
uspto-grants-1982_02
Patent number
US04316913

Reaction notes

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