Toluene → alpha-Cypermethrin 1-Epimeric Mixture

HRID 647458

Reaktionsgleichung

Reaktionsgleichung von HRID 647458
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].C1(C)C=CC=CC=1.C1(C(O)=O)CC1.C1(C)C=CC(S(O[CH:36]([C:50]#[N:51])[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:38]=2)(=O)=O)=CC=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:9][CH:36]([C:50]#[N:51])[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:38]=2)=[O:8])[C:5]1([CH3:10])[CH3:11]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 15655Cyclopropanecarboxylic acidHCID 41507Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acidHCID 12945136O-(p-toluenesulfonyl)-m-phenoxymandelonitrile

Produkt 1

HCID 9801977alpha-Cypermethrin 1-Epimeric Mixture

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (22 g, 0.105 M) was added to a solution of an inorganic base in water (50 ml). Toluene (100 ml), tetra-n-butylammonium bromide (1.6 g, 5 mole % based on the cyclopropane carboxylic acid) and alpha-cyano-3-phenoxybenzyl p-toluenesulphonate (37.9 g, 0.1 M) were added to the stirred mixture which was then heated at 40°-45° C. for 24 hours. The reaction mixture was then treated as in Example 1 to yield cis-alpha-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as a pale amber oil containing less than 1% trans-isomers.

Aufarbeitung

  1. additionwere added to the stirred mixture which
  2. temperaturewas then heated at 40°-45° C. for 24 hours
  3. additionThe reaction mixture was then treated as in Example 1

Quellen und Nachweise

ORD-Eintrag
ord-be7672de8d3b4f8ab12d14aaba57e654
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04409150

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