2-Methoxy-3-hydroxymethyl-5-ethyl-6-methylpyridine → 2-Methoxy-5-ethyl-6-methylnicotinaldehyde

HRID 273681Notes

Reaction equation

HRID 273681 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][C:6]([CH2:11][CH3:12])=[C:5]([CH3:13])[N:4]=1>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH3:13])[C:6]([CH2:11][CH3:12])=[CH:7][C:8]=1[CH:9]=[O:10]

Participants

4

Reactant 1

HCID 152284142-Methoxy-3-hydroxymethyl-5-ethyl-6-methylpyridine

Product 1

HCID 102616792-Methoxy-5-ethyl-6-methylnicotinaldehydeYield 90.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

Activated manganese dioxide (2.0 g) was added to a solution of 2-methoxy-3-hydroxymethyl-5-ethyl-6-methylpyridine (1.18 g, 6.5 mmol) in dry benzene (20 mL) and refluxed 5-10 hours. The warm suspension was filtered through a pad of anhydrous Na2SO4 and evaporated to yield 1.05 g (90%) of a viscous oil which solidified.

Workup

  1. temperaturerefluxed 5-10 hours
  2. filtrationThe warm suspension was filtered through a pad of anhydrous Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-d2bbc18a1e6b40b2ae6c5fe1e46175bf
Source dataset
uspto-grants-1995_02
Patent number
US05387512

Reaction notes

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