Sodium → 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile

HRID 1701665Notes

Reaction equation

HRID 1701665 reaction equation
Br[CH:2]([CH2:9][C:10]([Cl:13])([Cl:12])Cl)[C:3]([CH3:8])([CH3:7])[CH2:4][C:5]#[N:6].[Na]>C(O)C>[C:5]([CH:4]1[C:3]([CH3:7])([CH3:8])[CH:2]1[CH:9]=[C:10]([Cl:12])[Cl:13])#[N:6]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 233480014-Bromo-6,6,6-trichloro-3,3-dimethylhexanenitrile

Product 1

HCID 128981733-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 3-bromo-1-cyano-2,2-dimethyl-5,5,5-trichloropentane (0.5 g.) and a solution of sodium (0.2 g.) in ethanol (10 ml.) is refluxed for 2 hours after which the ethanol is removed by evaporation under reduced pressure. The residue is partitioned between chloroform (20 ml.) and water (20 ml.) and the chloroform layer separated, washed with water and dried over anhydrous magnesium sulphate. Removal of the solvent by evaporation under reduced pressure yields 1-cyano 2-(2,2,-dichlorovinyl)-3,3-dimethylcyclopropane, identified by infra-red and nuclear magnetic resonance spectroscopy.

Workup

  1. customis removed by evaporation under reduced pressure
  2. customThe residue is partitioned between chloroform (20 ml.) and water (20 ml.)
  3. customthe chloroform layer separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customRemoval of the solvent
  7. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-7756ac3e1c684e74a64a56e1b88dda1e
Source dataset
uspto-grants-1980_03
Patent number
US04195033

Reaction notes

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