Sodium Cyanide → 2-(Hydroxyimino)-2-phenylacetonitrile

HRID 1156159Notes

Reaction equation

HRID 1156159 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCl.[C-:12]#[N:13].[Na+].[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl.O>[N:8](=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]#[N:13])[OH:9]

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 12143(Z)-Benzaldehyde oximeHCID 14798Sodium HydroxideHCID 24526Chlorine

Product 1

HCID 699982-(Hydroxyimino)-2-phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent3×

Procedure

To 9.07 g (75 mmol) of benzaldoxime in 25 ml of carbon tetrachloride is added dropwise, at 5°, a solution of 45 ml of carbon tetrachloride saturated with 5.6 g (79 mmol) of chlorine gas. The mixture is stirred for 1 hour in an ice bath and then excess HCl is removed by vacuum. A saturated solution of 7.35 g (150 mmol) of sodium cyanide in water is added dropwise, at 0°. The mixture is stirred for 2 hours as it is allowed to warm to RT. An excess of aqueous sodium hydroxide is added and then the carbon tetrachloride layer is discarded. The aqueous layer is acidified and filtered, and the resulting solid is washed with water and dried to give α-oximinophenylacetonitrile, m.p.=120°-125°.

Workup

  1. customexcess HCl is removed by vacuum
  2. stirringThe mixture is stirred for 2 hours as it
  3. filtrationfiltered
  4. washthe resulting solid is washed with water
  5. customdried

Sources & evidence

ORD record
ord-e1bcfb0ba7a4409c8e72f5a395ebdd4f
Source dataset
uspto-grants-1982_06
Patent number
US04334087

Reaction notes

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