Butyl Chloride → 2-(3-Phenoxyphenyl)hexanenitrile

HRID 1863002Notes

Reaction equation

HRID 1863002 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Cl)[CH2:18][CH2:19][CH3:20].[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]([CH2:17][CH2:18][CH2:19][CH3:20])[C:12]#[N:13])[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8005Butyl ChlorideHCID 14798Sodium HydroxideHCID 40075m-Phenoxybenzyl cyanide

Product 1

HCID 234689332-(3-Phenoxyphenyl)hexanenitrileYield 54.8%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Into a three-necked 500 ml round-bottom flask are charged 35 g (0.17 mole) of m-phenoxybenzyl cyanide, 16.3 g (0.17 mole) of butyl chloride 4 g of tetraethylammonium bromide. To this mixture is added 27 g (0.34 mole) of 50% sodium hydroxide solution dropwise with stirring. The reaction mixture is heated at 90° for three hours. It is then poured into water and extracted with hexane. The combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 39 g of crude product. Vacuum distillation (149°-155°/0.2 mm) provides 24.7 g of pure product.

Workup

  1. temperatureThe reaction mixture is heated at 90° for three hours
  2. extractionextracted with hexane
  3. washThe combined hexane extracts are washed with water
  4. dry with materialdried over MgSO4
  5. customSolvent is evaporated
  6. customto give 39 g of crude product
  7. distillationVacuum distillation (149°-155°/0.2 mm)

Sources & evidence

ORD record
ord-cd0730cc712c4338ae854e988300bbda
Source dataset
uspto-grants-1979_09
Patent number
US04167576

Reaction notes

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