Sodium Cyanide → Cypermethrin

HRID 1155006Notes

Reaction equation

HRID 1155006 reaction equation
COCCOCCOC.O.[C-:11]#[N:12].[Na+].[O:14]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl:29][C:30]([Cl:40])=[CH:31][CH:32]1[CH:34]([C:35](Cl)=[O:36])[C:33]1([CH3:39])[CH3:38]>COCCOCCOC>[Cl:29][C:30]([Cl:40])=[CH:31][CH:32]1[CH:34]([C:35]([O:25][CH:24]([C:11]#[N:12])[C:23]2[CH:26]=[CH:27][CH:28]=[C:21]([O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:22]=2)=[O:36])[C:33]1([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 94551Permethric chlorideHCID 86618275Diglyme water

Product 1

HCID 2912CypermethrinYield 104.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A reaction flask was cooled to 0° and charged with 20 ml of diethylene glycol dimethyl ether/water solution (1/1 by volume) and sodium cyanide (0.78 g, 0.016 mole). The resultant solution was stirred, and 3-phenoxybenzaldehyde (1.98 g, 0.01 mole) was added in 5 ml of diethylene glycol dimethyl ether. 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (2.73 g, 0.012 mole) was added dropwise to the stirred reaction mixture at 20° over a 10 minute period. Stirring was continued for 2 hours. The reaction mixture was then extracted three times with 15 ml portions of diethyl ether, once with 15 ml of water, once with a 2 N solution of aqueous sodium hydroxide, three times with water (15 ml), dried over magnesium sulfate, and concentrated under reduced pressure to afford α-cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (4.35 g, 90% pure glpc).

Workup

  1. temperatureA reaction flask was cooled to 0°
  2. extractionThe reaction mixture was then extracted three times with 15 ml portions of diethyl ether
  3. dry with materialonce with 15 ml of water, once with a 2 N solution of aqueous sodium hydroxide, three times with water (15 ml), dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4183b92e226142c29a0df73e19be9f27
Source dataset
uspto-grants-1981_11
Patent number
US04299776

Reaction notes

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