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

HRID 1837
Notes
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Reaction equation

HRID 1837 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 136165902-(3,4-Dichlorophenyl)-2-hydroxyacetonitrileYield 100.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

25 g of 3,4-dichlorobenzaldehyde are added to a solution of 32.5 g of Na2S2O5 in 100 ml of water and the mixture is heated at 40°-45° C. for 1 hour. After one night at room temperature, the reaction mixture is cooled and a solution of 19.5 g of KCN in 40 ml of water is added slowly. After stirring for 30 minutes at RT, extraction is carried out with ether and the extract is washed with water, dried over MgSO4 and evaporated under vacuum to give 29 g of the expected product, which is used as such in the next step.

Workup

  1. temperaturethe mixture is heated at 40°-45° C. for 1 hour
  2. waitAfter one night at room temperature
  3. temperaturethe reaction mixture is cooled
  4. extractionextraction
  5. washthe extract is washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-2ed9fcf75bbf4af59779e91e6297c949
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726313

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes