Water → 4-(Oxoacetyl)benzonitrile

HRID 1784698Notes

Reaction equation

HRID 1784698 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[OH2:13]>CS(C)=O>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([CH:8]=[O:13])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 962WaterHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 212986014-(Oxoacetyl)benzonitrileYield 64.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-cyanophenacyl bromide (11.20 g, 49.99 mmol) in dimethylsulfoxide (83 mL) was treated with water (0.90 mL, 49.99 mmol). After stirring for 24 h at room temperature, it was poured into ice-water, and extracted with ether. The organic layer was washed with water and then brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by a silica gel column chromatography eluting 20-50% ethyl acetate in hexane to afford 4-cyanophenylglyoxal (5.10 g, 64.1%) as a yellow solid.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cf025574da9c425ca0c750432e9a196e
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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