Pyridine → alpha-Cypermethrin 1-Epimeric Mixture

HRID 1660513

Reaktionsgleichung

Reaktionsgleichung von HRID 1660513
[C:1]([CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1)[OH:4])#[N:2].[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].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:18][C:19]([Cl:29])=[CH:20][C@@H:21]1[C@H:23]([C:24]([O:4][CH:3]([C:1]#[N:2])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:6]=2)=[O:25])[C:22]1([CH3:27])[CH3:28]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chloride

Produkt 1

HCID 9801977alpha-Cypermethrin 1-Epimeric MixtureAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 468.6 g (2.08 moles) (cyano)(3-phenoxyphenyl)methanol and 2500 ml toluene was placed in a flask and heated to 40° C. During an 80-85 minute period, 509 g (2.24 moles) of (cis)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride prepared as described in Step B, and 186 g (2.35 moles) of pyridine were added under nitrogen. Upon completion of the addition, the reaction mixture was stirred 2.5 hours at 40° C. After cooling, the reaction mixture was washed successively with 1000 ml of water, 1000 ml of 1 N hydrochloric acid, 1000 ml of 1 N sodium hydroxide, twice with water, and once with an aqueous solution of sodium chloride. After being dried over magnesium sulfate, the solution was filtered through Celite and the solvent stripped using a rotary evaporator. Residual solvent was removed in a vacuum oven. A total of 918.3 g of 93.6% (cyano)(3-phenoxyphenyl)methyl cis-3-(2,2dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate was obtained.

Aufarbeitung

  1. customwas placed in a flask
  2. additionwere added under nitrogen
  3. additionUpon completion of the addition
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed successively with 1000 ml of water, 1000 ml of 1 N hydrochloric acid, 1000 ml of 1 N sodium hydroxide, twice with water
  6. dry with materialAfter being dried over magnesium sulfate
  7. filtrationthe solution was filtered through Celite
  8. customa rotary evaporator
  9. customResidual solvent was removed in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-6950a2ed40db4e91ae825f4b665310af
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04308279

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