Phenol → 4-Phenoxy-3-pyridinecarboxaldehyde

HRID 1588176Notes

Reaction equation

HRID 1588176 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[CH:21]=[O:22]>CN(C=O)C.[Cu]>[O:7]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[CH:21]=[O:22])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 140466744-Chloropyridine-3-carbaldehyde

Product 1

HCID 143264184-Phenoxy-3-pyridinecarboxaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of phenol (1.34 g, 14.3 mmol) in DMF (25 ml) was stirred with anhydrous potassium carbonate (0.99 g, 7.2 mmol) at 70°-80° C. for 40 minutes. 4-Chloro-3-pyridinecarboxaldehyde (2.02 g, 14.3 mmol) and copper bronze powder (0.10 g) were added and the resulting suspension stirred at 100°-110° C. for 2 hours. The reaction mixture was cooled, filtered and the residues washed with ether. The combined ether washings were diluted to 400 ml with more ether, washed with saturated brine (4×) and the solvent removed to give 4-phenoxy-3-pyridinecarboxaldehyde as a pale yellow crystalline solid (2.62 g); melting point 74°-75° C.; infrared max (nujol) 1590, 1695, 2760 cm-1 ; 1H NMR delta (CDCl3) 6.75 (1H broad), 7.15 (2H,d), 7.35 (1H,t), 7.50 (2H,t), 8.5-9.7 (2H,broad), 10.7 (1H,s).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe residues washed with ether
  4. additionThe combined ether washings were diluted to 400 ml with more ether
  5. washwashed with saturated brine (4×)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-25d2ad0c5d5446edb2d64d186bedb4ba
Source dataset
uspto-grants-1993_06
Patent number
US05221316

Reaction notes

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