Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester → Permethrin

HRID 1764542

Reaktionsgleichung

Reaktionsgleichung von HRID 1764542
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)(=[O:3])[CH3:2].C[C:20]1(C)[CH:22]([CH:23]=[C:24]([Cl:26])[Cl:25])[CH:21]1[C:27](OCC)=O>CCO.CCO.CCO.CCO.[Ti].C1(C)C=CC=CC=1>[CH3:20][C:21]1([CH3:27])[CH:22]([CH:23]=[C:24]([Cl:26])[Cl:25])[CH:2]1[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)=[O:3]

Komponenten

5

Edukt 2

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl esterHCID 170904Benzenemethanol, 3-phenoxy-, 1-acetate

Produkt 1

HCID 40326Permethrin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724286Titanium(IV)ethoxideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 24.2 parts of m-phenoxybenzyl acetate, 28.4 parts of ethyl 2,2-dimethyl-3-(2'-,2'-dichlorovinyl)-cyclopropanecarboxylate (cis:trans ratio, 58/42) and 1.3 parts of tetraethyl titanate in 200 parts of dry toluene was stirred and heated at the boiling point. The azeotrope of ethyl acetate and toluene was removed by distillation at the rate of 50 parts per hour while maintaining the reaction volume by the addition of fresh toluene. After 4 hours 5 parts of water were added and precipitated titanium dioxide removed by filtration. The toluene was then removed by heating under reduced pressure and 0.3 mm. of mercury. Volatile fractions removed were 9.0 parts of unreacted ethyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxylate, boiling at 75°-80° and 6.3 parts of unchanged m-phenoxybenzyl acetate, boiling at 125°-135°. There was obtained 26.85 parts of m-phenoxybenzyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate (cis trans ratio, 44/56).

Aufarbeitung

  1. temperatureheated at the boiling point
  2. customThe azeotrope of ethyl acetate and toluene was removed by distillation at the rate of 50 parts per hour
  3. temperaturewhile maintaining the reaction volume
  4. additionby the addition of fresh toluene
  5. additionAfter 4 hours 5 parts of water were added
  6. customprecipitated titanium dioxide
  7. customremoved by filtration
  8. customThe toluene was then removed
  9. temperatureby heating under reduced pressure and 0.3 mm
  10. customVolatile fractions removed

Quellen und Nachweise

ORD-Eintrag
ord-daa2ef472f4e464d83b46f5b155f5e89
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04116998

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