Potassium Hydroxide → Permethric acid

Reaktionsgleichung

[CH3:1][C:2]1([CH3:15])[CH:4]([CH2:5][C:6](Cl)([Cl:8])[Cl:7])[CH:3]1[C:10]([O:12]CC)=[O:11].[OH-].[K+]>>[CH3:1][C:2]1([CH3:15])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:10]([OH:12])=[O:11]

Komponenten

Edukt 2

HCID 14797Potassium Hydroxide

HCID 108413Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2,2,2-trichloroethyl)-, ethyl ester

Produkt 1

HCID 91658Permethric acid

Versuchsvorschrift

Ethyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)-cyclopropanecarboxylate was hydrolyzed with caustic potash to give 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane-carboxylic acid, and was converted into the diastereomeric (+)-octyl ester, which was analyzed by gas chromatography. The results were: (+)-cis, 83.6%; (-)-cis, 3.9%; (+)-trans, 7.5% (-)-trans, 5.0%. The e.e. was calculated to be 91% for the cis isomer and 20% for the trans isomer.

Quellen und Nachweise

ORD-Eintrag: ord-f734c0c5ffe6488f8fc76b57c1c23812
Quelldatensatz: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04552972

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