Hydrochloric Acid → Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid
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
Procedure
Potassium tertiary butoxide (0.45 mmol) 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 with CDCl3. NMR analysis showed a virtually quantitative yield of the desired cis acid.
Workup
- extractionextracted with CDCl3
Sources & evidence
- ORD record
- ord-b102740ead354a6093c5147df0213cf9
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04398032
Reaction notes
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