Benzyl Chloride → 4-Benzyloxybenzonitrile

HRID 522521Notes

Reaction equation

HRID 522521 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[OH-].[K+].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 130194-CyanophenolHCID 14797Potassium Hydroxide

Product 1

HCID 5613714-BenzyloxybenzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Treated a solution of 4-hydroxybenzonitrile (5.0 g, 42 mmol) in DMF (20 mL) with 2M KOH (21 mL, 42 mmol) followed by benzyl chloride (3.46 mL, 42 mmol). Heated in an oil bath at 80° C. for 2 h. Cooled to room temperature and poured onto water (100 mL). Filtered the resulting solid, washed with water (2×25 mL) and dried to obtain 4-benzyloxy-benzonitrile (5.1 g) as a solid.

Workup

  1. temperatureCooled to room temperature
  2. additionpoured onto water (100 mL)
  3. filtrationFiltered the resulting solid
  4. washwashed with water (2×25 mL)
  5. customdried

Sources & evidence

ORD record
ord-8e8e171ce07f4771ab518a87712aa6bc
Source dataset
uspto-grants-2016_05
Patent number
US09334246B2

Reaction notes

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