Water → HCID 21465360, compound

HRID 1939948Notes

Reaction equation

HRID 1939948 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].[H-].[Na+].Br[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15].O>CN(C)C=O>[CH3:17][O:16][C:14]([CH:13]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 119072-HydroxybenzonitrileHCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionate

Product 1

HCID 21465360HCID 21465360, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Cyanophenol (1.0 g, 8.39 mmol) was dissolved in N,N-dimethylformamide (5 ml), and 60% sodium hydride (0.40 g, 10 mmol) was added thereto under ice-cooling, followed by stirring for one hour. Methyl (±)-2-bromopropionate (1.03 ml, 9.23 mmol) was added to the mixture followed by stirring at room temperature for one night. After the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried, the drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 2-[1-(methoxycarbonyl)ethoxy]benzonitrile (1.70 g, 99%).

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring at room temperature for one night
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic layer was dried
  6. filtrationthe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-560270ad52eb473d96a8114cddb4c738
Source dataset
uspto-grants-1997_12
Patent number
US05698560

Reaction notes

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