4-Hydroxybenzaldehyde → 2-(4-formylphenoxy)acetonitrile

HRID 1506146Notes

Reaction equation

HRID 1506146 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:13][C:14]#[N:15].[Cl-].[NH4+]>CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:13][C:14]#[N:15])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 27644042-(4-formylphenoxy)acetonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-Hydroxybenzaldehyde (244 mg, 2.00 mmol) in N,N-dimethylformamide (5 mL) was mixed with sodium hydride (60 wt % dispersion in liquid paraffin, 120 mg, 3.00 mmol) and chloroacetonitrile (189 μL, 3.00 mmol) under cooling with ice and then stirred at 50° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with 1M aqueous sodium hydroxide, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a brown oil (128 mg, yield 40%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 1M aqueous sodium hydroxide
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b418d20dcb4a41ec908be761d97dd05a
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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