Butyl Chloride → 2-(2-Phenoxyphenyl)hexanenitrile

HRID 1613258Notes

Reaction equation

HRID 1613258 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+]>CS(C)=O.O>[CH2:19]([CH:13]([C:1]#[N:2])[C:12]1[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

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

Product 1

HCID 197756142-(2-Phenoxyphenyl)hexanenitrileYield 86.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Into a 300 ml three-necked flask equipped with a stirrer, a condenser, a thermometer and an addition funnel are charged 50 ml of dimethyl sulfoxide and 7.4 g (0.15 mole) of sodium cyanide. A solution of 30 g (0.14 mole) of o-phenoxybenzyl chloride in 10 ml of dimethyl sulfoxide is added dropwise at room temperature. The reaction mixture is stirred for 11/2 hours. Butyl chloride (18.7 g, 0.14 mole) is then added to the reaction mixture followed by dropwise addition of 34.3 g (0.43 mole) of 50% sodium hydroxide solution. Reaction temperature increased to 52° after the addition and stirring is continued for 1 hour. The reaction mixture is then diluted with 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 product. The product can be further purified by vacuum distillation (b.p. 137-142/0.2 mm).

Workup

  1. customInto a 300 ml three-necked flask equipped with a stirrer, a condenser
  2. customReaction temperature
  3. temperatureincreased to 52°
  4. additionafter the addition
  5. stirringstirring
  6. waitis continued for 1 hour
  7. extractionextracted with hexane
  8. washThe combined hexane extracts are washed with water
  9. dry with materialdried over MgSO4
  10. customSolvent is evaporated

Sources & evidence

ORD record
ord-7f1804e591594598a9bed0fc2e75250b
Source dataset
uspto-grants-1993_03
Patent number
US05192783

Reaction notes

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