Water → Cypermethrin

HRID 1155003Notes

Reaction equation

HRID 1155003 reaction equation
[C-:1]#[N:2].[Na+].O.[O:5]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:20][C:21]([Cl:31])=[CH:22][CH:23]1[CH:25]([C:26](Cl)=[O:27])[C:24]1([CH3:30])[CH3:29]>O1CCCC1>[Cl:20][C:21]([Cl:31])=[CH:22][CH:23]1[CH:25]([C:26]([O:16][CH:15]([C:1]#[N:2])[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([O:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:13]=2)=[O:27])[C:24]1([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 94551Permethric chloride

Product 1

HCID 2912CypermethrinYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of sodium cyanide (2.40 g, 0.049 mole) in a 1:1 by volume mixture of water and tetrahydrofuran (50 ml) at 15° was added dropwise over 30 minutes a mixture of 3-phenoxybenzaldehyde (7.00 g, 0.035 mole) and 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (10.00 g, 0.042 mole). Stirring was continued at 15° for an additional 2 hours, after which the reaction mixture was extracted thrice with methylene chloride (40 ml each). The combined organic layers were washed once with aqueous 2 N NaOH (50 ml), four times with waer (50 ml portions) to a final wash pH of about 6, then dried over MgSO4 and concentrated to give α-cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (13.9 g, 95.5% yield).

Workup

  1. additionwas added dropwise over 30 minutes
  2. extractionafter which the reaction mixture was extracted thrice with methylene chloride (40 ml each)
  3. washThe combined organic layers were washed once with aqueous 2 N NaOH (50 ml), four times with waer (50 ml portions) to
  4. washa final wash pH of about 6
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af624339540e4f59820ad1578d2b5e9b
Source dataset
uspto-grants-1981_11
Patent number
US04299776

Reaction notes

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