Water → 4-Ethylphenylacetonitrile

HRID 1082250Notes

Reaction equation

HRID 1082250 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].O>CS(C)=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 3

HCID 962WaterHCID 8929Sodium CyanideHCID 122315601-(Bromomethyl)-4-ethylbenzene

Product 1

HCID 1428674-EthylphenylacetonitrileYield 93.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-ethylbenzyl alcohol (2.72 g, 20 mmol, purchased from Aldrich) and 50 ml of 47% hydrobromic acid (purchased from Wako Junyaku Kogyo) was stirred vigorously for 30 minutes at room temperature. The reaction mixture was extracted with hexane to give 3.98 g of 4-ethylbenzyl bromide as a colorless oil. Then to a hot solution (50° C.) of sodium cyanide (1.96 g, 40 mmol) in 20 ml of dimethyl sulfoxide was added the above 3.98 g of 4-ethylbenzyl bromide and the mixture was stirred for 3 hours at ambient temperature. To the resultant reaction mass was added water and extracted with hexane. The solvent was removed to give 2.70 g (yield: 93.1%) of 4-ethylphenylacetonitrile as a pale yellow oil.

Workup

  1. customTo the resultant reaction mass
  2. extractionextracted with hexane
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-be46bfd1231b47a98dac8a8d9cd4f176
Source dataset
uspto-grants-1996_12
Patent number
US05589506

Reaction notes

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