Hydrochloric Acid → Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid

HRID 67280

Reaction equation

HRID 67280 reaction equation
CC(C)([O-])C.[K+].[Cl:7][CH:8]([Cl:18])[CH:9]1[CH:14]2[CH:12]([C:13]2([CH3:16])[CH3:15])[C:11](=[O:17])[O:10]1.Cl>CS(C)=O.O>[Cl:7][C:8]([Cl:18])=[CH:9][C@H:14]1[C:13]([CH3:16])([CH3:15])[C@H:12]1[C:11]([OH:17])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 204929844-Dichloromethyl-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 41507Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. extractionextracted CDCl3

Sources & evidence

ORD record
ord-78c9fa680c9548668ca5189c8a5276c2
Source dataset
uspto-grants-1982_08
Patent number
US04346038

Linked notes

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