Sodium Cyanide → 4-Ethylphenylacetonitrile

HRID 1900092Notes

Reaction equation

HRID 1900092 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)[CH3:5]>CS(C)=O.O>[CH2:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][C:1]#[N:2])=[CH:8][CH:7]=1)[CH3:5]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 122315601-(Bromomethyl)-4-ethylbenzene

Product 1

HCID 1428674-EthylphenylacetonitrileYield 93.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2.72 g (20.0 mmol) of 4-ethylbenzyl alcohol (purchased from Aldrich) and 50 ml of 47% hydrobromic acid (purchased from Wako Junyaku Kogyo) was stirred at room temperature for 30 minutes vigorously and extracted with hexane to give 3.98 g of 4-ethylbenzyl bromide as a colorless oil. Subsequently, to a solution of 1.96 g (40.0 mmol) of sodium cyanide (purchased from Kokusan Kagaku) in 20 ml of dimethyl sulfoxide (purchased from Aldrich) heated at 50 ° C. was added 3.98 g of the above 4-ethylbenzylbromide, the solution was stirred at ambient temperature for 3 hours, the resultant reaction mass was dissolved in water and extracted with hexane, and hexane was removed to give 2.70 g (yield: 93.1%) of 4-ethylphenylacetonitrile as a light yellow oil.

Workup

  1. customthe resultant reaction mass
  2. extractionextracted with hexane, and hexane
  3. customwas removed

Sources & evidence

ORD record
ord-e5efe2db7a8a4ce18e4ce31f66a25a06
Source dataset
uspto-grants-1996_11
Patent number
US05574062

Reaction notes

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