(4-(Pyridin-2-yloxymethyl)-phenyl)-methanol → 4-((Pyridin-2-yloxy)methyl)benzaldehyde

HRID 640082Notes

Reaction equation

HRID 640082 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59255473(4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

Product 1

HCID 592551184-((Pyridin-2-yloxy)methyl)benzaldehydeYield 42%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-(pyridin-2-yloxymethyl)-phenyl)methanol (1.9 g, 8.6 mmol) described in Manufacturing Example 2-1-1 and methylene chloride (30 mL) was added manganese dioxide (15 g, 17 mmol) at room temperature, which was stirred overnight at that temperature. The reaction mixture was filtered through a Celite pad, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (770 mg, 42%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. customthe solvent was evaporated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4)

Sources & evidence

ORD record
ord-d7c3e305657c4f9c9ad07219e510453f
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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