Toluene → alpha-Cypermethrin 1-Epimeric Mixture

HRID 647457

反応式

HRID 647457 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 9801977alpha-Cypermethrin 1-Epimeric Mixture収率 99%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4add32f706d6482bb574c4d3955c5caa
出典データセット
uspto-grants-1983_10
特許番号
US04409150

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