Dimethylformamide → 4-Benzylphenylacetonitrile

HRID 439776Notes

Reaction equation

HRID 439776 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-4c1ecbddd4414acc87fc0d9410bce41b
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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