Trimethylsilyl cyanide → 2-Hydroxy-2-(4-isobutylphenyl)acetonitrile

HRID 249156Notes

Reaction equation

HRID 249156 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C[Si]([C:17]#[N:18])(C)C>[I-].[Zn+2].[I-]>[OH:10][CH:9]([C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:12][CH:11]=1)[C:17]#[N:18]

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 577537Benzaldehyde, 4-(2-methylpropyl)-

Product 1

HCID 190247872-Hydroxy-2-(4-isobutylphenyl)acetonitrileYield 107.5%

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

Zinc iodide (0.21 g) was added to a mixture of 4-isobutylbenzaldehyde (6.5 g) and trimethylsilylcyanide (5.0 g). The mixture was stirred at room temperature for 3 minutes and partitioned between ethyl acetate and 7% hydrochloric acid. The organic layer was washed with 7% hydrochloric acid and water and dried over magnesium sulfate. The solvent was removed in vacuo to give 2-hydroxy-2-(4-isobutylphenyl)acetonitrile as a yellow oil (8.15 g).

Workup

  1. custompartitioned between ethyl acetate and 7% hydrochloric acid
  2. washThe organic layer was washed with 7% hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9efbf3dd78584800a75988f8512e6324
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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