Potassium Carbonate → 4-(4-Formylphenoxy)benzonitrile

HRID 1470649Notes

Reaction equation

HRID 1470649 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 6138064-(4-Formylphenoxy)benzonitrileYield 112%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 4-cyanophenol (1.24 g, 10.4 mmol), potassium carbonate (3.3 g, 23.9 mmol), and 4-fluoro benzaldehyde (1.0 g, 8 mmol) in dry DMF (50 mL) was stirred at 100° C. overnight under nitrogen atmosphere. After the reaction is completed it was cooled to room temperature and poured in to ice cold water. The mixture was extracted with ethyl acetate (100 mL×2), the combined organic layers were washed with water (50 mL×2), and brine, then dried over anhydrous sodium sulphate and concentrated. The residue was purified by column chromatography using 3% ethyl acetate in hexane to obtain the title compound (2 g, 86%)

Workup

  1. additionpoured in to ice cold water
  2. extractionThe mixture was extracted with ethyl acetate (100 mL×2)
  3. washthe combined organic layers were washed with water (50 mL×2), and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f76ef61a0fae403587c8e67ac46540f4
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

Loading…