Water → 6-Phenoxypyridine-2-carbaldehyde

HRID 1703347Notes

Reaction equation

HRID 1703347 reaction equation
[O:1]([CH:8](OC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)C1C=CC=CC=1.S(=O)(=O)(O)O.O>O1CCOCC1>[O:15]([C:11]1[N:10]=[C:9]([CH:8]=[O:1])[CH:14]=[CH:13][CH:12]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 12833252HCID 12833252, compound

Product 1

HCID 129410066-Phenoxypyridine-2-carbaldehydeYield 111.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.5 g of 2-[bis-(phenoxy)methyl]-6-(phenoxy)pyridine in 15 ml of 1,4-dioxane was added dropwise, 5 percent sulfuric acid until the mixture just became turbid. The mixture was heated over a steam bath at 80°-90° C. for about 10 minutes. The reaction mixture was poured into 20 ml of water, producing a yellowish emulsion and then extracted with 50 ml of ethyl ether. The extract was washed with 50 ml of a 5 percent aqueous sodium hydroxide solution and thrice with 50 ml portions of water and then with 50 ml of a saturated sodium chloride solution. The extract was then dried over sodium sulfate and the solvent removed by evaporation under reduced pressure. The residue was a yellow-orange oil which solidified partially on cooling to yield 0.3 g of the desired product. The product was confirmed by Infrared and Nuclear Magnetic resonance analysis.

Workup

  1. temperatureThe mixture was heated over a steam bath at 80°-90° C. for about 10 minutes
  2. customproducing a yellowish emulsion
  3. extractionextracted with 50 ml of ethyl ether
  4. washThe extract was washed with 50 ml of a 5 percent aqueous sodium hydroxide solution and thrice with 50 ml portions of water
  5. dry with materialThe extract was then dried over sodium sulfate
  6. customthe solvent removed by evaporation under reduced pressure
  7. temperatureon cooling

Sources & evidence

ORD record
ord-0b492d7e732d477f8265e9a94f1a979d
Source dataset
uspto-grants-1982_09
Patent number
US04351943

Reaction notes

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