3-Benzyloxy-6-hydroxymethyl-2-methylpyridine → HCID 12397262, compound

HRID 1606308Notes

Reaction equation

HRID 1606308 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[N:11][C:12]([CH2:15][OH:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[N:11][C:10]=1[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 123972613-Benzyloxy-6-hydroxymethyl-2-methylpyridine

Product 1

HCID 12397262HCID 12397262, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 19.4 g. (0.0846 mol) of 3-benzyloxy-6-hydroxymethyl-2-methylpyridine (liberated from the hydrochloride salt) and 100 g. of manganese dioxide in 800 ml. of chloroform is refluxed with vigorous stirring for three hours. The mixture is filtered and the chloroform is evaporated to give a yellow oil which is chromatographed on alumina, eluting with chloroform. The recovered material is purified through its hydrochloride salt and reconverted to the base, 5-benzyloxy-6-methyl-2-pyridinecarboxaldehyde, m.p. 62°-63°C.

Workup

  1. additionA mixture of 19.4 g
  2. filtrationThe mixture is filtered
  3. customthe chloroform is evaporated
  4. customto give a yellow oil which
  5. customis chromatographed on alumina
  6. washeluting with chloroform
  7. customThe recovered material is purified through its hydrochloride salt

Sources & evidence

ORD record
ord-9a5a7dcd443a435da8621cc0270c01ba
Source dataset
uspto-grants-1976_04
Patent number
US03952101

Reaction notes

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