Water → 3-(4-Benzyloxyphenyl)propionitrile

HRID 850460Notes

Reaction equation

HRID 850460 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]#[N:11])=[CH:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 870793-(p-Hydroxyphenyl)propiononitrile

Product 1

HCID 103541463-(4-Benzyloxyphenyl)propionitrileYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-(4-Hydroxyphenyl)propionitrile (1.47 g, 0.01 mol) was dissolved in DMF (24 ml), and to this solution were successively added benzyl bromide (1.31 ml, 0.011 mol, 1.1 eq) and anhydrous potassium carbonate (4.15 g, 0.030 mol, 3.0 eq). The mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and water (100 ml) was added. The mixture was extracted twice with ethyl acetate (100 ml). The organic layers were combined, washed with saturated brine (200 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(4-benzyloxyphenyl)propionitrile (2.39 g, 100%) as a colorless solid.

Workup

  1. temperatureThis reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted twice with ethyl acetate (100 ml)
  3. washwashed with saturated brine (200 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d7341f2ca2942ef83d27fedcb44ac5e
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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