2,6-Dichlorobenzaldehyde → 55931-21-0

HRID 374591Notes

Reaction equation

HRID 374591 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[O:5].[C-:11]#[N:12].[K+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]([OH:5])[C:11]#[N:12]

Participants

5

Reactant 2

HCID 67372,6-DichlorobenzaldehydeHCID 9032Potassium Cyanide

Product 1

HCID 1309356455931-21-0Yield 86.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred and cooled suspension of 438 g of 2,6-dichlorobenzaldehyde in 2000 g of glacial acetic acid there was added dropwise a solution of 203 g of potassium cyanide in 350 g of water, keeping the temperature below 25° C. Stirring was continued overnight at room temperature. The reaction mixture was concentrated and the residue, which solidified upon cooling, was filtered off and dried, yielding 438 g of (±)-2,6-dichloro-α-hydroxybenzeneacetonitrile; mp. 90° C. (interm. 1).

Workup

  1. temperaturecooled
  2. customthe temperature below 25° C
  3. stirringStirring
  4. concentrationThe reaction mixture was concentrated
  5. temperatureupon cooling
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-ae400d15e8984894a0b10b8b7f10af93
Source dataset
uspto-grants-1996_01
Patent number
US05480997

Reaction notes

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