4-Hydroxybenzaldehyde → 4-(Pyridin-2-yloxy)benzaldehyde

HRID 1891955Notes

Reaction equation

HRID 1891955 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[H-].[Na+]>CN(C)C=O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 97462-FluoropyridineHCID 24758Sodium hydride

Product 1

HCID 37552924-(Pyridin-2-yloxy)benzaldehydeYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To an N,N-dimethylformamide solution (100 mL) of 4-hydroxybenzaldehyde (10 g, 82 mmol) and 2-fluoropyridine (8.0 g, 82 mmol) was added sodium hydride (3.3 g, 82 mmol, 60% in oil), which was stirred for 30 minutes at 120° C., then for 45 minutes at 140° C., and then for 2 hours at 160° C. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water (three times), and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (9.3 g, 57%).

Workup

  1. waitfor 45 minutes at 140° C.
  2. waitfor 2 hours at 160° C
  3. temperatureThe mixture was cooled to room temperature
  4. custompartitioned into ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water (three times)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-4fd8ed11e812415199768143c441dfe5
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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