Thionyl Chloride → cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chloride

HRID 443768

Reaction equation

HRID 443768 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].S(Cl)([Cl:15])=O>>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([Cl:15])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 41507Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid

Product 1

HCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideYield 98%

Procedure

In a flask were placed 400 g (1.913 moles) of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and sufficient thionyl chloride to create a slurry. The remainder of the thionyl chloride (total used was 412.6 g (5.74 moles)) was added dropwise with stirring under a nitrogen blanket, and the reaction mixture was stirred at room temperature overnight. The crude product was distilled at 66°-67° C. at 66.7 Pa (0.5 mm of Hg) to produce 426.4 g of 98% (cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride.

Workup

  1. customIn a flask were placed
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. distillationThe crude product was distilled at 66°-67° C. at 66.7 Pa (0.5 mm of Hg)

Sources & evidence

ORD record
ord-c8518b69332747b4b7c6a46f157c9f3d
Source dataset
uspto-grants-1981_04
Patent number
US04261921

Linked notes

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