4-Hydroxybenzaldehyde → 4-(Pyridin-3-yloxy)benzaldehyde

HRID 2413358Notes

Reaction equation

HRID 2413358 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 12679Hexamethylphosphoramide

Product 1

HCID 46774194-(Pyridin-3-yloxy)benzaldehydeYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 g of 3-bromopyridine, 20 g of 4-hydroxybenzaldehyde, 60 g of potassium carbonate and 150 ml of hexamethylphosphoramide was heated at a temperature of 130° to 135° C. for 11 hours. After cooling, the mixture was poured into water and extracted with diethyl ether. The ether extract was washed with water and extracted with 10% hydrochloric acid. The aqueous layer was washed with diethyl ether, rendered alkaline with sodium hydroxide and extracted with diethyl ether. The ether extract was washed with water and dried over sodium sulfate. The solvent was distilled off and the resulting oily substance was purified by silica gel chromatography (eluted with diethyl ether) to obtain 13.9 g (45% yield) of 4-(3-pyridyloxy)benzaldehyde as a colorless oil having a boiling point of 135°-140° C./2-3 mmHg.

Workup

  1. temperaturewas heated at a temperature of 130° to 135° C. for 11 hours
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. extractionextracted with 10% hydrochloric acid
  7. washThe aqueous layer was washed with diethyl ether
  8. extractionextracted with diethyl ether
  9. extractionThe ether extract
  10. washwas washed with water
  11. dry with materialdried over sodium sulfate
  12. distillationThe solvent was distilled off
  13. customthe resulting oily substance was purified by silica gel chromatography (eluted with diethyl ether)

Sources & evidence

ORD record
ord-e6131201c0644d65ad6c891fc8499abd
Source dataset
uspto-grants-1985_01
Patent number
US04496735

Reaction notes

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