Water → 2-Benzyloxyphenylacetonitrile

HRID 850457Notes

Reaction equation

HRID 850457 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:11]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 105828242-(2-Hydroxyphenyl)acetonitrile

Product 1

HCID 5612222-BenzyloxyphenylacetonitrileYield 120.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(2-Hydro xyphenyl)acetonitrile (1.01 g, 0.0076 mol) was dissolved in DMF (10 ml), and to this solution were successively added benzyl bromide (0.90 ml, 0.0076 mol, 1.0 eq) and anhydrous potassium carbonate (2.1 g, 0.015 mol, 3.0 eq). The mixture was stirred with heating at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and water (10 ml) was added. The mixture was extracted twice with ethyl acetate (30 ml). The organic layers were combined, washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give (2-benzyloxyphenyl)acetonitrile (2.04 g, 100%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted twice with ethyl acetate (30 ml)
  3. washwashed with saturated brine (60 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-65b7b6d8a6394ec7a3867682c8823ee2
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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