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Ethanol → 1-(3-Cyanophenyl)-2-hydroxy-2-[4-(methylthio)phenyl]-ethanone

HRID 2231129
Notes
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Reaction equation

HRID 2231129 reaction equation
[C-]#N.[Na+].C(O)C.[C:7]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])#[N:8].[CH3:17][S:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1>O>[C:7]([C:9]1[CH:10]=[C:11]([C:12](=[O:13])[CH:23]([OH:24])[C:22]2[CH:25]=[CH:26][C:19]([S:18][CH3:17])=[CH:20][CH:21]=2)[CH:14]=[CH:15][CH:16]=1)#[N:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 769854-(Methylthio)benzaldehydeHCID 90670m-Formylbenzonitrile

Product 1

HCID 184635761-(3-Cyanophenyl)-2-hydroxy-2-[4-(methylthio)phenyl]-ethanoneYield 61%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

Sodium cyanide (3 mmol, 0.147 g) was added to a mixture of ethanol (30 ml), water (30 ml), 3-cyanobenzaldehyde (30 mmol, 3.93 g) and 4-(methylthio)benzaldehyde (30 mmol, 4.0 ml). The reaction was stirred at reflux 30 minutes, diluted with water (20 ml) and extracted with ethyl acetate (250 ml). The organic layer was separated, dried over magnesium sulfate, concentrated, and the residue purified by silica gel chromatography (2:1 hexane:ethyl acetate), affording the title compound as a solid (5.2, 61%).

Workup

  1. temperatureat reflux 30 minutes
  2. extractionextracted with ethyl acetate (250 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue purified by silica gel chromatography (2:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-931871adcd0c47b69681659acaf9fdd5
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06426360B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes