Reaction #8716

ord-ce3fd0b48b39417c9f1ac902d61127bf

Reaction equation

N#Cc1ccccc1O
2-hydroxylbenzonitrile
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCBr
ethyl bromide
→
CCOc1ccccc1C#N
colorless liquid
Yield 97.1%
CCOc1ccccc1C#N
2-Ethoxy-benzonitrile
Yield 97.1%

Reactants

N#Cc1ccccc1O
2-hydroxylbenzonitrile
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCBr
ethyl bromide

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureunder reflux overnight
  2. 2
    FiltrationThe solid is filtered off
  3. 3
    Otherthe solvent is removed in vacuo
  4. 4
    workup.DISTILLATIONthe residue is distilled in vacuo

Procedure

25 g (210 mmol) of 2-hydroxylbenzonitrile are heated, together with 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide, in 500 ml of acetone under reflux overnight. The solid is filtered off, the solvent is removed in vacuo and the residue is distilled in vacuo. 30.0 g (97%) of a colorless liquid are obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091203B2uspto-grants-2006_08