Sodium Cyanide → Cypermethrin

HRID 851075Notes

Reaction equation

HRID 851075 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:16]#[N:17].[Na+].[Cl:19][C:20]([Cl:30])=[CH:21][CH:22]1[C:24]([CH3:26])([CH3:25])[CH:23]1[C:27](Cl)=[O:28]>O.C1CCCCC1>[Cl:19][C:20]([Cl:30])=[CH:21][CH:22]1[C:24]([CH3:26])([CH3:25])[CH:23]1[C:27]([O:12][CH:11]([C:16]#[N:17])[C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)=[O:28]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 94551Permethric chloride

Product 1

HCID 2912Cypermethrin

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8078CyclohexaneSolvent2×

Procedure

A 500 ml. round-bottomed flask equipped with a stirrer operating at 500 rpm was charged with 0.2 mole of 3-phenoxybenzaldehyde, 20 ml. of water, 15.2 g. of sodium cyanide, 90 ml. of cyclohexane and a catalyst (if any). 0.2 mole of 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropanecarbonyl chloride was added at 15°-20° over 30 minutes, followed by 10 ml. of cyclohexane. The mixture thus formed was stirred at 15°-20° C. At the end of the reaction, 100 ml. of water were added and the organic phase was filtered, washed with 100 ml. of water and the cyclohexane was then removed on a rotary evaporator. The catalysts used and the results obtained are shown in Table 1.

Workup

  1. customround-bottomed flask equipped with a stirrer
  2. customThe mixture thus formed
  3. customAt the end of the reaction, 100 ml
  4. filtrationthe organic phase was filtered
  5. washwashed with 100 ml
  6. customof water and the cyclohexane was then removed on a rotary evaporator
  7. customthe results obtained

Sources & evidence

ORD record
ord-a3ca5af674334ccd891eefd4575c9c19
Source dataset
uspto-grants-1983_05
Patent number
US04382894

Reaction notes

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