Sodium Hydroxide → 3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid

HRID 904748

Reaktionsgleichung

Reaktionsgleichung von HRID 904748
C([O:3][C:4]([CH:6]1[CH:8]([CH:9]=[C:10]([Br:12])[Br:11])[C:7]1([CH3:14])[CH3:13])=[O:5])C.[OH-].[Na+]>>[CH3:13][C:7]1([CH3:14])[CH:8]([CH:9]=[C:10]([Br:12])[Br:11])[CH:6]1[C:4]([OH:5])=[O:3]

Komponenten

3

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 12550018HCID 12550018, Verbindung

Produkt 1

HCID 1812483-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acidAusbeute 92 %

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

36.2 g. of 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester (purity: 90%, cis) trans ratio: 45:65/, 4 g. of a 25% aqueous sodium hydroxide solution and 0.2 g. of tricaprylmethyl ammonium chloride are stirred at 100° C. for 30 minutes, whereupon three 4-g. portions of the sodium hydroxide solution are added in 30 minutes intervals and stirring is continued for altogether 240 minutes. The mixture is cooled to 20° C., diluted with 100 ml. of water and extracted with 10 ml. of benzene. The aqueous solution is admixed with 12 g. of a 36% aqueous hydrochloric acid solution at 70° C. and cooled to room temperature with stirring. The precipitated acid is dissolved in 60 ml. of benzene, the solution is separated and the solvent is evaporated. 30.0 g (92%) of 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropanecarboxylic acid are obtained. Cis/trans ratio: 40:60.

Aufarbeitung

  1. additiondiluted with 100 ml
  2. extractionof water and extracted with 10 ml
  3. temperatureof a 36% aqueous hydrochloric acid solution at 70° C. and cooled to room temperature
  4. stirringwith stirring
  5. dissolutionThe precipitated acid is dissolved in 60 ml
  6. customof benzene, the solution is separated
  7. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5896fab0aaf848b38c252d58a0650131
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04419524

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