Dimethylformamide → 4-Benzylphenylacetonitrile

HRID 1654701Notes

Reaction equation

HRID 1654701 reaction equation
[CH2:1]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Cl)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[C-]#N.[Na+].[CH3:24][N:25](C=O)C>C(OCC)(=O)C>[CH2:1]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12][C:24]#[N:25])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 84334Benzene, 1-(chloromethyl)-4-(phenylmethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 5975314-Benzylphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzylbenzyl chloride (198.34 g) in dimethylchloride (DMF) (50 ml) was added in turn sodium hydrogen carbonate (76.88 g) and sodium cyanide (56.07 g). In that case, the solution was cooled as occasion demands, since heat is slightly generated. After stirring at room temperature for 17 hours, DMF (100 ml) was further added. After stirring at room temperature for 67 hours, ethyl acetate (300 ml) was added, and the precipitate was filtered, washed with ethyl acetate (300 ml). The filtrate and the washings were combined, washed with saturated aqueouse sodium chloride solution (20 ml×4), dried over anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (189.69 g).

Workup

  1. temperatureIn that case, the solution was cooled as occasion demands
  2. temperaturesince heat
  3. stirringAfter stirring at room temperature for 67 hours
  4. filtrationthe precipitate was filtered
  5. washwashed with ethyl acetate (300 ml)
  6. washwashed with saturated aqueouse sodium chloride solution (20 ml×4)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-baf799d6036b470ebd16cdd14f1468d7
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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