Sodium Cyanide → alpha-Cypermethrin 1-Epimeric Mixture

HRID 126682

Reaktionsgleichung

Reaktionsgleichung von HRID 126682
[C-]#N.[Na+].[CH:4]1([NH:10]CCCS(O)(=O)=O)CCCCC1.[Cl:18][C:19]([Cl:29])=[CH:20][C@@H:21]1[C@H:23]([C:24](Cl)=[O:25])[C:22]1([CH3:28])[CH3:27].[O:30]([C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH:40]=[O:41])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O.CCCCCCC>[Cl:18][C:19]([Cl:29])=[CH:20][C@@H:21]1[C@H:23]([C:24]([O:41][CH:40]([C:4]#[N:10])[C:39]2[CH:42]=[CH:43][CH:44]=[C:37]([O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:38]=2)=[O:25])[C:22]1([CH3:28])[CH3:27]

Komponenten

7

Edukt 4

HCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 708153-(Cyclohexylamino)-1-propanesulfonic acidHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chloride

Produkt 1

HCID 9801977alpha-Cypermethrin 1-Epimeric Mixture

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

A stirred mixture of sodium cyanide (18.0 g, 0.36 mole) and 3-(cyclohexylamino)propanesulfonic acid (1.34 g, 0.006 mole) in 300 ml of water was warmed to 40°. During a one hour period, maintaining a reaction temperature of about 40°, a solution of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (71.7 g, 0.315 mole) and 3-phenoxybenzaldehyde (61.9 g, 0.3 mole) in 262.2 g of n-heptane was added. The mixture was then stirred at 40° for one additional hour, after which it was washed with an aqueous solution containing 20% sodium carbonate and then with water. The organic phase was separated from the mixture and the solvent removed by distillation under reduced pressure to give α-cyano-3-phenoxybenzyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate.

Aufarbeitung

  1. temperaturewas warmed to 40°
  2. temperaturemaintaining a reaction temperature of about 40°
  3. washafter which it was washed with an aqueous solution
  4. additioncontaining 20% sodium carbonate
  5. customThe organic phase was separated from the mixture
  6. customthe solvent removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-92d69f50b91f450fb5744ced5dbdbe85
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254051

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