Permethric acid → Cypermethrin

HRID 848047Notes

Reaction equation

HRID 848047 reaction equation
O=P1([O:10][CH:11]([C:25]#[N:26])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)OCC(C)(C)CO1.[Na].[Cl:28][C:29]([Cl:39])=[CH:30][CH:31]1[CH:33]([C:34](O)=[O:35])[C:32]1([CH3:38])[CH3:37]>O>[O:18]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH:11]([O:10][C:34]([CH:33]1[CH:31]([CH:30]=[C:29]([Cl:28])[Cl:39])[C:32]1([CH3:38])[CH3:37])=[O:35])[C:25]#[N:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 91658Permethric acidHCID 5360545SodiumHCID 20566133HCID 20566133, compound

Product 1

HCID 2912CypermethrinYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of 38 g of 2-oxo-2-(3-phenoxy-α-cyanobenzyloxy)-5,5-dimethyl-1,3,2-dioxa-phosphorinane, 26 g of the sodium salt of 3-(2,2-dichloro-vinyl)-2,2-dimethylcyclopropane-1-carboxylic acid and 260 g of diglycol dimethyl ether was heated to 150° C. for 20 hours, while stirring. After cooling, the mixture was poured into water and the product was extracted with ligroin. The ligroin phase was washed 3 times with water and dried over sodium sulphate. After filtration, the ligroin was distilled off from the filtrate in vacuo and the residue was subjected to incipient distillation under a high vacuum. 32 g (77% of theory) of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid 3-phenoxy-α-cyano-benzyl ester were obtained as the residue.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with ligroin
  3. washThe ligroin phase was washed 3 times with water
  4. dry with materialdried over sodium sulphate
  5. filtrationAfter filtration
  6. distillationthe ligroin was distilled off from the filtrate in vacuo
  7. distillationthe residue was subjected to incipient distillation under a high vacuum

Sources & evidence

ORD record
ord-c1f05675be474e19809bf93689c53dd1
Source dataset
uspto-grants-1981_10
Patent number
US04294762

Reaction notes

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