4,5-Bis(phenylmethoxy)-2-pyridinemethanol → 4,5-Bis(benzyloxy)picolinaldehyde

HRID 1252618Notes

Reaction equation

HRID 1252618 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([CH2:23][OH:24])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(C)=O.[O-2].[O-2].[Mn+4]>[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][N:12]=[C:11]([CH:23]=[O:24])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 141825004,5-Bis(phenylmethoxy)-2-pyridinemethanol

Product 1

HCID 141825014,5-Bis(benzyloxy)picolinaldehydeYield 55.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 0.54 g (1.7 mmol) of 4,5-bis(phenylmethoxy)-2-pyridinemethanol in 15 ml of acetone was added 1.5 mg (17 mmol) of manganese dioxide and the mixture was stirred overnight at room temperature. The mixture was then filtered over a silica gel column (70-250 mesh), and the aldehyde eluated with acetone. Evaporation of the eluent and trituration of the residue with petroleum ether furnished 0.3 g of the title compound, melting point 104.3° C.

Workup

  1. filtrationThe mixture was then filtered over a silica gel column (70-250 mesh)
  2. customEvaporation of the eluent and trituration of the residue with petroleum ether

Sources & evidence

ORD record
ord-14b4a1124ed94c19b91eaf69b0b56e77
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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