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

HRID 1737565Notes

Reaction equation

HRID 1737565 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-624d52a93ef74b259a98079d2a505e45
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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