Thionyl Chloride → 3-[2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride
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][CH:4]1[CH:6]([C:7]([Cl:21])=[O:8])[C:5]1([CH3:11])[CH3:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4.2 g (0.0147 mole) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropane-carboxylic acid were dissolved in 50 ml of carbon tetrachloride, and 8.8 g of thionyl chloride were slowly added dropwise at 40° C., whilst stirring. The mixture was then heated under reflux for 4 hours. At the end of the 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. 4.0 g (89.7% of theory) of (+)-trans-Z-(3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropane-carboxylic acid chloride were obtained as a crystalline solid with a melting point of 65°-70° C. ##STR12##
Workup
- temperatureThe mixture was then heated
- temperatureunder reflux for 4 hours
- distillationAt the end of the reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum
- 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-0a890368593e4ad784d04ef932bf0051
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04772629
Reaction notes
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