4-Hydroxybenzaldehyde → 4-[2-(4-Formylphenoxy)ethyl]benzonitrile

HRID 1595476Notes

Reaction equation

HRID 1595476 reaction equation
CS([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)(=O)=O.O[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:21]([C:20]1[CH:23]=[CH:24][C:17]([O:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:18][CH:19]=1)=[O:22]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 226326484-Cyanophenethyl methanesulfonate

Product 1

HCID 229887784-[2-(4-Formylphenoxy)ethyl]benzonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8.55 g (38 mmole) 4-cyanophenethyl methanesulfonate, 4.64 g (38 mmole) p-hydroxybenzaldehyde and 18.7 g (57 mmole) cesium carbonate in 150 ml acetonitrile was refluxed over night. The salt was filtered off and the solvent evaporated in vacuo. The residue was treated with 2 M sodium hydroxide and dichloromethane. The organic phase was dried and evaporated in vacuo. Purification by chromatography on silica gel using dichloromethane as eluent gave 1.6 g (yield 17%) of 4-[2-(4-formylphenoxy)ethyl]benzonitrile.

Workup

  1. filtrationThe salt was filtered off
  2. customthe solvent evaporated in vacuo
  3. additionThe residue was treated with 2 M sodium hydroxide and dichloromethane
  4. customThe organic phase was dried
  5. customevaporated in vacuo
  6. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-c62ee2638ad74940a3e8f76c123c1540
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

Loading…