Methanol → (2-Chloro-6-methoxypyridin-4-yl)methanol

HRID 279602Notes

Reaction equation

HRID 279602 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4](Cl)[N:3]=1.[OH-:11].[Na+].[CH3:13]O>>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([O:11][CH3:13])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 11457961(2-Chloro-6-methoxypyridin-4-yl)methanolYield 28%

Procedure

A mixture of 2,6-dichloro-4-hydroxymethylpyridine (1.72 g, 16 mmol) and 40% aqueous sodium hydroxide solution (5 ml) in methanol (50 ml) was heated at reflux for 24 hours. The mixture was allowed to cool and the volatiles removed by evaporation. The residue was extracted with ethyl acetate and the solvent removed from the extracts by evaporation. The residue was recrystallised from ethyl acetate/hexane to give 2-chloro-4-hydroxymethyl-6-methoxypyridine (490 mg, 28%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureto cool
  4. customthe volatiles removed by evaporation
  5. extractionThe residue was extracted with ethyl acetate
  6. customthe solvent removed from the extracts by evaporation
  7. customThe residue was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1ff18e1a6af445d2b647f58eeda5bb4f
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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