Thionyl Chloride → HCID 53680508, compound

HRID 848762Notes

Reaction equation

HRID 848762 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[C:6]([O:11][CH3:12])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:13](O)=[O:14].S(Cl)([Cl:19])=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[C:6]([O:11][CH3:12])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:13]([Cl:19])=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54323314HCID 54323314, compound

Product 1

HCID 53680508HCID 53680508, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

8.7 g (0.0365 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid were dissolved in 100 ml of carbon tetrachloride, and 21 g of thionyl chloride were slowly added dropwise at 60° 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. The residue was distilled in vacuo. 6 g (64.2% of theory) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid chloride were obtained as a slightly yellow liquid with a boiling point of 80° C./2 mbar.

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. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-16ec1e3b80c84cdcb58119aa97e293c5
Source dataset
uspto-grants-1981_10
Patent number
US04297366

Reaction notes

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