Toluene → alpha-Cypermethrin 1-Epimeric Mixture

HRID 647456

反応式

HRID 647456 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 97.3%

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 (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.

後処理

  1. customprepared
  2. additionwere added to the stirred mixture which
  3. temperatureThe mixture was cooled to ambient temperature
  4. customthe organic phase was separated off
  5. washwashed with aqueous potassium carbonate solution (2×200 ml) and water (2×200 ml)
  6. customevaporated
  7. customdegassed under vacuum

出典と根拠

ORDレコード
ord-bb5b25184ed94f6b82d54a5d9de5e618
出典データセット
uspto-grants-1983_10
特許番号
US04409150

関連ノート

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