Sodium Cyanide → Cypermethrin

HRID 1155004Notes

Reaction equation

HRID 1155004 reaction equation
O1CCOCC1.[C-:7]#[N:8].[Na+].[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:25][C:26]([Cl:36])=[CH:27][CH:28]1[CH:30]([C:31](Cl)=[O:32])[C:29]1([CH3:35])[CH3:34]>O>[Cl:25][C:26]([Cl:36])=[CH:27][CH:28]1[CH:30]([C:31]([O:21][CH:20]([C:7]#[N:8])[C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:18]=2)=[O:32])[C:29]1([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 312751,4-DioxaneHCID 382843-PhenoxybenzaldehydeHCID 94551Permethric chloride

Product 1

HCID 2912CypermethrinYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction flask, charged with 25 ml 1,4-dioxane and a solution of sodium cyanide (2.4 g, 0.049 mole) in 25 ml water, was cooled to 0°. To the flask was added 3-phenoxybenzaldehyde (7 g, 0.035 mole) in one portion, with stirring. 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (10 g, 0.042 mole) was added dropwise over a period of 30 minutes. The temperature of the mixture was maintained between 0° and 5°, and stirring was continued for one hour after the acyl chloride had been added. The reaction mixture was then extracted three times with 50 ml portions of diethyl ether. After phase separation, the combined organic layers were washed once with a 2 N aqueous sodium hydroxide solution, three times with 50 ml portions of water, dried over magnesium sulfate, and concentrated under reduced pressure to afford α-cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (11.8 g, 81% yield).

Workup

  1. temperatureThe temperature of the mixture was maintained between 0° and 5°
  2. stirringstirring
  3. extractionThe reaction mixture was then extracted three times with 50 ml portions of diethyl ether
  4. customAfter phase separation
  5. washthe combined organic layers were washed once with a 2 N aqueous sodium hydroxide solution, three times with 50 ml portions of water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31b37958f9fc43d09f43a5a04fb29e14
Source dataset
uspto-grants-1981_11
Patent number
US04299776

Reaction notes

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