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

HRID 863418Notes

Reaction equation

HRID 863418 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 6 N HCl to dissolve the magnesium salts. The turbid solution is extracted with CHCl3, and the organic layer is washed with 0.1 N 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 6 N HCl
  5. dissolutionto dissolve the magnesium salts
  6. extractionThe turbid solution is extracted with CHCl3
  7. washthe organic layer is washed with 0.1 N 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-bea0d5a8ba80491bb4bcebdaf3e735d2
Source dataset
uspto-grants-1998_02
Patent number
US05721240

Reaction notes

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