Butyl Chloride → 2-(2-Phenoxyphenyl)hexanenitrile

HRID 1862996Notes

Reaction equation

HRID 1862996 reaction equation
[C-:1]#[N:2].[Na+].[O:4]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:19](Cl)[CH2:20][CH2:21][CH3:22].[OH-].[Na+]>O.CS(C)=O>[O:4]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]([CH2:19][CH2:20][CH2:21][CH3:22])[C:1]#[N:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 8005Butyl ChlorideHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 169302Benzene, (chloromethyl)phenoxy-

Product 1

HCID 197756142-(2-Phenoxyphenyl)hexanenitrileYield 92.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Into a three-necked 300 ml round-bottom flask are charged 7.4 g (0.15 mole) of sodium cyanide and 80 ml of dimethyl sulfoxide. To this slurry is added 30 g (0.13 mole) of 2-phenoxybenzyl chloride dropwise. Reaction temperature increases from 24° to 44° C. The reaction mixture is stirred for an additional 11/2 hours. To this reaction mixture is added 13.7 g (0.13 mole) of butyl chloride followed by dropwise addition of 34 g (0.4 mole) of 50% sodium hydroxide solution. After stirring for an additional 1/2 hour, reaction mixture is poured into 150 ml of water and extracted with hexane. The combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 32 g of a crude product. Material can be further purified by vacuum distillation (bp 149-60/0.25 mm).

Workup

  1. customReaction temperature
  2. temperatureincreases from 24° to 44° C
  3. stirringAfter stirring for an additional 1/2 hour
  4. customreaction mixture
  5. extractionextracted with hexane
  6. washThe combined hexane extracts are washed with water
  7. dry with materialdried over MgSO4
  8. customSolvent is evaporated

Sources & evidence

ORD record
ord-2009824e844c4711864ee132d75c55a3
Source dataset
uspto-grants-1979_09
Patent number
US04167576

Reaction notes

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