Potassium Cyanide → 2-(3,4-Dichlorophenyl)-2-hydroxyacetonitrile

HRID 1957041Notes

Reaction equation

HRID 1957041 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=[O:6].[C-:11]#[N:12].[K+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C:11]#[N:12])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 136165902-(3,4-Dichlorophenyl)-2-hydroxyacetonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 70 g of 3,4-dichlorobenzaldehyde and 90 g of Na2S2 O5 in 300 ml of water is stirred overnight at RT. The reaction mixture is cooled to 0° C., a solution of 52 g of KCN in 100 ml of water is added dropwise and the reaction mixture is stirred while the temperature is allowed to rise to RT. It is extracted with ether, the organic phase is washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 76 g of the expected product, which is used as such.

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred while the temperature
  3. customto rise to RT
  4. extractionIt is extracted with ether
  5. washthe organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-c8d6e0c87ab94a3989fb38353a2af180
Source dataset
uspto-grants-1998_07
Patent number
US05780466

Reaction notes

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