1R-cis-Permethrinic acid → Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid
Reaction equation
[CH3:1][C:2]1([CH3:12])[C@H:4]([C:5]([OH:7])=[O:6])[C@@H:3]1[CH:8]=[C:9]([Cl:11])[Cl:10]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[C@@H:4]([C:5]([OH:7])=[O:6])[C@H:3]1[CH:8]=[C:9]([Cl:10])[Cl:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
100 g. of dl-cis-trans-permethric acid (consisting of 40% cis and 60% trans isomer) were stirred with 400 ml. of benzene at 27° for one hour, then the suspension was filtered. The solid product, i.e. 31 g. of permethric acid consisting of 79% cis and 21% trans isomer was worked up according to the Example (4b) for obtaining racemic cis-permethric acid. The benzene solution was evaporated to give 67.2 g. of a mixture consisting of 23% cis and 77% trans isomer which was then stirred together with extraction petroleum ether at 30° C. for 5 hours. The suspension was filtered to give 26.8 g. of dl-trans-permethric acid as a solid product containing more than 95% trans isomer.
Workup
- filtrationthe suspension was filtered
Sources & evidence
- ORD record
- ord-36300baa177d444b86df7e574bb87abb
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04599444
Reaction notes
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