Toluene → alpha-Cypermethrin 1-Epimeric Mixture

HRID 647457

반응식

HRID 647457 반응식
[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]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 41507Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acidHCID 12945136O-(p-toluenesulfonyl)-m-phenoxymandelonitrile

생성물 1

HCID 9801977alpha-Cypermethrin 1-Epimeric Mixture수율 99%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

Cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (1680 g, 8.04 M) was added to a solution of potassium carbonate (555 g, 4.02 M) in water (3800 ml). Toluene (7600 ml), tetra-n-butylammonium bromide (115 g, 0.4 M) and alpha-cyano-3-phenoxybenzyl p-toluenesulphonate (2902 g, 7.65 M; prepared as in Example 1(A) above) were added to the stirred mixture which was then heated at 70° C. for 5 hours. The mixture was cooled to ambient temperature and the organic phase was separated off, washed twice with aqueous potassium carbonate solution and twice with water, evaporated and degassed under vacuum to leave cis-alpha-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate as a yellow oil (3130 g, 99%), containing less than 1% trans-isomers.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe organic phase was separated off
  3. washwashed twice with aqueous potassium carbonate solution and twice with water
  4. customevaporated
  5. customdegassed under vacuum

출처 및 근거

ORD 기록
ord-4add32f706d6482bb574c4d3955c5caa
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04409150

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