Potassium Cyanide → 3-(3-Methoxy-4-methylphenyl)propyl cyanide

HRID 1859809Notes

Reaction equation

HRID 1859809 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([O:12][CH3:13])[CH:6]=1.[C-:14]#[N:15].[K+]>CC(C)=O.CCO.O>[CH3:13][O:12][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][C:14]#[N:15])[CH:10]=[CH:9][C:8]=1[CH3:11]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 186265044-(3-Bromopropyl)-2-methoxy-1-methylbenzene

Product 1

HCID 186265273-(3-Methoxy-4-methylphenyl)propyl cyanideYield 100%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 8.68 g (35.7 mmol) of 4-(3-bromopropyl)-2-methoxy-1-methylbenzene in 50 mL of acetone and 50 mL of EtOH was treated with a solution of 2.8 g (42.8 mmol) of KCN in 20 mL of H2O and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed with H2O, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 6.75 g (100% yield) of the product as an oil. The structure was confirmed by NMR and IR spectroscopy.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washwashed with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e599833520eb40b18de2ec28474f1937
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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