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

HRID 622724ノート

反応式

HRID 622724 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 30187603-[2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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##

後処理

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

出典と根拠

ORDレコード
ord-0a890368593e4ad784d04ef932bf0051
出典データセット
uspto-grants-1988_09
特許番号
US04772629

反応ノート

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