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

HRID 2267969Notes

Reaction equation

HRID 2267969 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.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.O1CCOCCOCCOCCOCCOCC1>[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

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 97462-FluoropyridineHCID 11430Potassium Carbonate

Product 1

HCID 37552924-(Pyridin-2-yloxy)benzaldehydeYield 45.2%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 36.7 grams (0.30 mole) of 4-hydroxybenzaldehyde, 12.9 mL (0.15 mole) of 2-fluoropyridine, and 41.0 grams (0.30 mole) of potassium carbonate, and 1.05 grams of 1,4,7,10,13,16-hexaoxacyclooctadecane in 200 mL of dimethyl sulfoxide was heated at 120° C. for four days. The reaction mixture was cooled to ambient temperature, and 500 mL of water was added. The organic and aqueous layers were separated. The aqueous layer was basified with aqueous 10% sodium hydroxide and extracted with two 400 mL portions of diethyl ether. The ether extracts were combined and washed with one 100 mL portion of aqueous 5% sodium hydroxide, followed by one 100 mL portion of aqueous 10% lithium chloride. The organic layer and extracts were combined, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to yield a residue, which was subjected to column chromatography on silica gel. Elution was accomplished with 15-20% acetone in petroleum ether mixtures. The product-containing fractions were combined and concentrated under reduced pressure, yielding 13.5 grams of 4-(pyrid-2-yloxy)benzaldehyde. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe organic and aqueous layers were separated
  3. extractionextracted with two 400 mL portions of diethyl ether
  4. washwashed with one 100 mL portion of aqueous 5% sodium hydroxide
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto yield a residue, which
  9. washElution
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-302e36e2136549d7a3d375f689bb6477
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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