Reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C1(C)C=CC(S(O[CH:36]([C:50]#[N:51])[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:38]=2)(=O)=O)=CC=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:9][CH:36]([C:50]#[N:51])[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:38]=2)=[O:8])[C:5]1([CH3:10])[CH3:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (199 g, 0.95 M) was added to a solution of potassium carbonate (65.6 g, 0.475 M) in water (450 ml). Toluene (900 ml), tetra-n-butylammonium bromide (13.5 g, 0.05 M) and alpha-cyano-3-phenoxybenzyl p-toluenesulphonate (341 g, 0.9 M; prepared as described in A above) were added to the stirred mixture which was then heated at 70° C. for 3 hours. The mixture was cooled to ambient temperature and the organic phase was separated off, washed with aqueous potassium carbonate solution (2×200 ml) and water (2×200 ml), evaporated and degassed under vacuum to leave cis-alpha-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as a pale amber oil (364 g, 97.3%), containing less than 1% trans-isomers.
Workup
- customprepared
- additionwere added to the stirred mixture which
- temperatureThe mixture was cooled to ambient temperature
- customthe organic phase was separated off
- washwashed with aqueous potassium carbonate solution (2×200 ml) and water (2×200 ml)
- customevaporated
- customdegassed under vacuum
Sources & evidence
- ORD record
- ord-bb5b25184ed94f6b82d54a5d9de5e618
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04409150
Linked notes
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