Pyridine → 2,2-Dimethyl-3-(1-isobutenyl)-cyclopropanecarboxylic acid 3-(2,2-dichlorovinyloxy)-alpha-cyanobenzyl ester

HRID 1578126Notes

Reaction equation

HRID 1578126 reaction equation
[Cl:1][C:2]([Cl:15])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[CH:8]([OH:11])[C:9]#[N:10].[CH3:16][C:17]1([CH3:27])[CH:19]([CH:20]=[C:21]([CH3:23])[CH3:22])[CH:18]1[C:24](Cl)=[O:25].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]([Cl:15])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[CH:8]([O:11][C:24]([CH:18]1[CH:19]([CH:20]=[C:21]([CH3:23])[CH3:22])[C:17]1([CH3:27])[CH3:16])=[O:25])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 26620(1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chlorideHCID 205689253-(2,2-Dichlorovinyloxy)mandelonitrile

Product 1

HCID 543575142,2-Dimethyl-3-(1-isobutenyl)-cyclopropanecarboxylic acid 3-(2,2-dichlorovinyloxy)-alpha-cyanobenzyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 9.8 g of 3-(2,2-dichlorovinyloxy)-mandelonitrile and 7.5 g of 2,2-dimethyl-3-(1-isobutenyl)-cyclopropanecarboxylic acid chloride in 100 cc toluene is added a solution of 3.5 g of pyridine in 200 ml toluene dropwise within 10 minutes. The resultant suspension is stirred for 15 hours at 20°-25° C., washed with dilute HCl and totally concentrated.

Workup

  1. washwashed with dilute HCl
  2. concentrationtotally concentrated

Sources & evidence

ORD record
ord-0940a55c6e5b4746b7bf283145617557
Source dataset
uspto-grants-1981_09
Patent number
US04291056

Reaction notes

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