Butyl Chloride → 2-(4-Phenylthiophenyl) hexanenitrile

HRID 128224

Reaction equation

HRID 128224 reaction equation
[C:1]1([S:7][C:8]2[CH:16]=[CH:15][C:11]([CH2:12][C:13]#[N:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17](Cl)[CH2:18][CH2:19][CH3:20].[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C.O>[C:1]1([S:7][C:8]2[CH:16]=[CH:15][C:11]([CH:12]([CH2:17][CH2:18][CH2:19][CH3:20])[C:13]#[N:14])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8005Butyl ChlorideHCID 14798Sodium Hydroxide2×HCID 238605[4-(Phenylsulfanyl)phenyl]acetonitrile

Product 1

HCID 544229802-(4-Phenylthiophenyl) hexanenitrileYield 65.1%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 41 g (0.18 mole) of 4-phenylthiobenzyl cyanide, 18 g (0.19 mole) of butyl chloride and 2 g of tetraethylammonium bromide is added 16 g (0.2 mole) of 50% sodium hydroxide solution dropwise at room temperature with stirring. The reaction mixture is heated at 85° for 1/2 hour and then an additional 16 g (0.2 mole) of 50% sodium hydroxide solution are added. Heating is continued for another 1/2 hour. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are washed with water, saturated sodium chloride solution and dried over MgSO4. Solvent is evaporated to give 47 g of a crude product. Vacuum distillation (173°-180°/0.05 mm) gives 33 g of pure product.

Workup

  1. temperatureThe reaction mixture is heated at 85° for 1/2 hour
  2. temperatureHeating
  3. extractionextracted with ether
  4. washThe combined ether extracts are washed with water, saturated sodium chloride solution
  5. dry with materialdried over MgSO4
  6. customSolvent is evaporated
  7. customto give 47 g of a crude product
  8. distillationVacuum distillation (173°-180°/0.05 mm)

Sources & evidence

ORD record
ord-1d8b680913c54b35923d1760dd742b70
Source dataset
uspto-grants-1981_03
Patent number
US04259339

Linked notes

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