Potassium Cyanide → Cypothrin

HRID 2420050Notes

Reaction equation

HRID 2420050 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.[CH3:16][C:17]1([CH3:31])[C:19]2([C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20]2)[CH:18]1[C:28](Cl)=[O:29].[C-:32]#[N:33].[K+]>O>[CH3:16][C:17]1([CH3:31])[C:19]2([C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20]2)[CH:18]1[C:28]([O:12][CH:11]([C:32]#[N:33])[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:29]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 382843-PhenoxybenzaldehydeHCID 1084583,3-Dimethylspiro[cyclopropane-1,1'-indene]-2-carbonyl chloride

Product 1

HCID 65491Cypothrin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.05 gram-mole of m-phenoxybenzaldehyde and 0.05 gram-mole of 3,3-dimethylspiro[cyclopropane-1,1'-indene]-2-carboxylic acid chloride is added slowly, portionwise, to a solution of 0.075 gram-mole of potassium cyanide in 100 ml of water at 5° C. the mixture is stirred for 1.5 hours at 5° and then extracted with three 50--ml portions of ether. The extracts are washed with 10% hydrochloric acid solution, saturated sodium bicarbonate solution, and water and then dried over sodium sulfate. Removal of the ether under vacuum leaves α-cyano-m-phenoxybenzyl 3,3-dimethylspiro[cyclopropane-1,1'-indene]-2-carboxylate as a yellow-brown oil which is a useful insecticide as taught in U.S. Pat. No. 3,966,959 (1976).

Workup

  1. additionis added slowly
  2. extractionextracted with three 50
  3. washThe extracts are washed with 10% hydrochloric acid solution, saturated sodium bicarbonate solution, and water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the ether under vacuum

Sources & evidence

ORD record
ord-dc7f9291608b4069bcee522a393ee05e
Source dataset
uspto-grants-1978_08
Patent number
US04108904

Reaction notes

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