Reaktion #95558

ord-78c9fa680c9548668ca5189c8a5276c2

Reaktionsgleichung

CC(C)(C)[O-].[K+]
Potassium tertiary butoxide
CC1(C)C2C(=O)OC(C(Cl)Cl)C21
4-dichloromethyl-6,6-dimethyl-3-oxabicyclo[3.1.0]-hexan-2-one
Cl
hydrochloric acid
→
CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)O
cis 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid

Edukte

CC(C)(C)[O-].[K+]
Potassium tertiary butoxide
CC1(C)C2C(=O)OC(C(Cl)Cl)C21
4-dichloromethyl-6,6-dimethyl-3-oxabicyclo[3.1.0]-hexan-2-one
Cl
hydrochloric acid

Reagenzien

Keine

Lösungsmittel

CS(C)=O
dimethylsulphoxide
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted CDCl3

Vorschrift

Potassium tertiary butoxide (0.45 mol) was added to a solution of 4-dichloromethyl-6,6-dimethyl-3-oxabicyclo[3.1.0]-hexan-2-one (0.16 mmol) in dry dimethylsulphoxide (0.4 ml) and stirred at room temperature for 1/2 hour. The solution was then diluted with water, acidified with concentrated hydrochloric acid and extracted CDCl3. NMR analysis showed a virtually quantitative yield of the desired cis acid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04346038uspto-grants-1982_08