3-(4-Benzyloxyphenyl)acrylonitrile → 3-(4-Benzyloxyphenyl)propionitrile

HRID 864984Notes

Reaction equation

HRID 864984 reaction equation
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]#[N:19])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]#[N:19])=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 39556983-(4-Benzyloxyphenyl)acrylonitrileHCID 5462224Magnesium

Product 1

HCID 103541463-(4-Benzyloxyphenyl)propionitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Magnesium turnings (28 g) are added to a solution of 3-(4-benzyloxyphenyl)-acrylonitrile (17.0 g, 72.3 mmol) in dry MeOH (800 mL). As soon as moderate H2 evolution is observed, the flask is immersed in an efficient ice/water cooling bath until the initially vigorous reaction subsides after about 45 minutes. Additional Mg (10 g) is added, and the reaction mixture is stirred for 4 hours with intermittent cooling during which time most of the Mg metal is consumed. The mixture is evaporated to a thick paste, which is then cooled to 0° C. and treated slowly with enough cold 6N HCl to dissolve the magnesium salts. The turbid solution is extracted with CHCl3, and the organic layer is washed with 0.1N NaOH and H2O, dried over Na2SO4, and evaporated to give white waxy solid residue that is recrystallized from EtOH/H2O (2:1) to give 3-(4-benzyloxyphenyl)-propionitrile.

Workup

  1. customthe flask is immersed in an efficient ice/water cooling bath until the initially vigorous reaction subsides after about 45 minutes
  2. customis consumed
  3. customThe mixture is evaporated to a thick paste, which
  4. additiontreated slowly with enough cold 6N HCl
  5. dissolutionto dissolve the magnesium salts
  6. extractionThe turbid solution is extracted with CHCl3
  7. washthe organic layer is washed with 0.1N NaOH and H2O
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customto give white waxy solid residue that
  11. customis recrystallized from EtOH/H2O (2:1)

Sources & evidence

ORD record
ord-01be360a6ffb48b5a18eeba1c37bdf2e
Source dataset
uspto-grants-1996_10
Patent number
US05565463

Reaction notes

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