Hydrogen Peroxide → 4-(Pyridin-2-yloxy)phenol

HRID 1837814Notes

Reaction equation

HRID 1837814 reaction equation
B(O)(O)O.[OH:5]O.S(=O)(=O)(O)O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19]1[CH:26]=[CH:25][C:22](C=O)=[CH:21][CH:20]=1>O1CCCC1>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19]1[CH:26]=[CH:25][C:22]([OH:5])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 37552924-(Pyridin-2-yloxy)benzaldehyde

Product 1

HCID 146523734-(Pyridin-2-yloxy)phenolYield 9.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Following Scheme I: To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 3.1 g (50.2 mmol) boric acid, 10 mL tetrahydrofuran, 2.3 mL (20 mmol) 30% hydrogen peroxide, and 1 mL concentrated sulfuric acid. To the reaction was added a solution of 2.0 g (10 mmol) 4-(pyridin-2-yloxy)-benzaldehyde in 10 mL tetrahydrofuran dropwise over 5 minutes. The reaction was stirred 3 hr at 60° C., cooled, filtered, and the filtrate neutralized with saturated aqueous sodium bicarbonate solution. The mixture was extracted into 2× ethyl acetate, and the organic layer washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 180 mg (9.6%) of the product as a solid.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionThe mixture was extracted into 2× ethyl acetate
  5. washthe organic layer washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-44bb32691a94416ba1d3abe808a842d6
Source dataset
uspto-grants-2004_08
Patent number
US06784299B2

Reaction notes

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