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

HRID 1420996Notes

Reaction equation

HRID 1420996 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-4bee39168aa442f6a6d428cb26501fb5
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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