Potassium Cyanide → 4-(7-Methoxy-1-naphthyl)butyronitrile

HRID 2888

Reaction equation

HRID 2888 reaction equation
[C-:1]#[N:2].[K+].S(O[CH2:9][CH2:10][CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[CH:15]=[CH:14][CH:13]=1)(=O)(=O)C>CS(C)=O>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[CH:14][CH:13]=[C:12]2[CH2:11][CH2:10][CH2:9][C:1]#[N:2])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 153368673-(7-Methoxy-1-naphthyl)propyl mesylate

Product 1

HCID 153368684-(7-Methoxy-1-naphthyl)butyronitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 100-cm3 flask, the 3-(7-methoxy-1-naphthyl)propyl mesylate obtained in stage D is dissolved in DMSO. KCN is added and the mixture is brought to reflux for 2 h. It is allowed to cool. It is poured into a water/ice mixture. The resulting mixture is extracted with ether. The organic phase is washed with water, dried over CaCl2 and evaporated. The product obtained is recrystallized.

Workup

  1. temperatureto reflux for 2 h
  2. temperatureto cool
  3. extractionThe resulting mixture is extracted with ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over CaCl2
  6. customevaporated
  7. customThe product obtained
  8. customis recrystallized

Sources & evidence

ORD record
ord-ebf01e6b38bc42c089b9940d05b2423f
Source dataset
uspto-grants-1998_03
Patent number
US05731352

Linked notes

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