Sodium Hydroxide → 3,4-Dimethoxy-2-pyridinemethanol

HRID 845537Notes

Reaction equation

HRID 845537 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][N:9]=1)(=O)C>>[OH:6][CH2:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 106085512-Acetoxymethyl-3,4-dimethoxypyridine

Product 1

HCID 107258093,4-Dimethoxy-2-pyridinemethanolYield 96%

Procedure

After adding 15 ml of 2N sodium hydroxide solution, 4.8 g of 2-acetoxymethyl-3,4-dimethoxypyridine are stirred vigorously at 80° C., whereupon a homogeneous solution forms from the initial two-phase mixture. After 2 hours, the solution is allowed to cool and is extracted five times with 30 ml of methylene chloride each time, the combined organic phases are washed twice with 5 ml of 0.3N sodium hydroxide solution each time, dried over potassium carbonate, filtered and concentrated and the distillation residue is stirred with petroleum ether. 3.6 g (96% of theory) of 2-hydroxymethyl-3,4-dimethoxy-pyridine are obtained as a colorless solid of m.p. 87°-89° C.

Workup

  1. temperatureto cool
  2. extractionis extracted five times with 30 ml of methylene chloride each time
  3. washthe combined organic phases are washed twice with 5 ml of 0.3N sodium hydroxide solution each time
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3a9ea89d0a9c4fed80343e175ebbdb91
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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