Thionyl Chloride → rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

HRID 848770Notes

Reaction equation

HRID 848770 reaction equation
[Cl:1]/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:3]\[C@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].S(Cl)([Cl:21])=O>C(Cl)(Cl)(Cl)Cl>[Cl:1]/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:3]\[C@H:4]1[C@H:6]([C:7]([Cl:21])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22820830rel-(1R,3S)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 44152741rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chlorideYield 96.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1.0 g (0.0035 mol) of (±)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid were dissolved in 20 ml of carbon tetrachloride, and 5 ml of thionyl chloride were added dropwise slowly 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 at a bath temperature of 60° C./2 mm Hg. 1.03 g (96.9% of theory) of (±)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid chloride were obtained as an oily liquid. ##STR21##

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 at a bath temperature of 60° C./2 mm Hg

Sources & evidence

ORD record
ord-90c4267b33b840dc91ebb9f529a132b5
Source dataset
uspto-grants-1981_10
Patent number
US04297371

Reaction notes

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