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

HRID 1384616Notes

Reaction equation

HRID 1384616 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%). 1H NMR Spectrum: (DMSOd6) 3.80(s, 3H); 4.45(d, 2H); 5.45(t, 1H); 6.70(s, 1H); 6.98(s, 1H)

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-454298aa0f50402eac3cc5d6b289b6dc
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

Loading…