Sodium Hydroxide → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

HRID 486818Notes

Reaction equation

HRID 486818 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH3:16])[C:11]([CH3:17])=[CH:10][N:9]=1)(=O)C.CC1C(C)=C(OC)C(C)=C[N+]=1[O-]>>[OH:6][CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH3:16])[C:11]([CH3:17])=[CH:10][N:9]=1

Participants

4

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 50672892-(Acetoxymethyl)-4-methoxy-3,5-dimethylpyridineHCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxide

Product 1

HCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridineYield 92.4%

Procedure

30% aqueous sodium hydroxide was added over a solution of crude 2-acetoxymethyl-3,5-dimethyl-4-methoxypyridine prepared from 30.06 g (0.18 mole) of 2,3,5-trimethyl-4-methoxypyridine N-oxide, to pH 13. The mass was stirred for about 3.5 hours at 25°-28° C., with addition of 30% aqueous sodium hydroxide at the appropriate rate to hold the pH to between 11.7 and 13. Once the reaction was terminated (complete disappearance of the band located towards 1700 cm-1) the pH was adjusted to 6.5 with acetic acid, water was added and the mass was extracted with methylene chloride. The solvent was removed by vacuum distillation and finally 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine was distilled at 142°-145° C. (9 torr.) as a colourless liquid which crystallised on standing. 27.23 g were obtained. Yield 92.4%.

Workup

  1. customOnce the reaction was terminated (complete disappearance of the band
  2. additionwas added
  3. extractionthe mass was extracted with methylene chloride
  4. customThe solvent was removed by vacuum distillation and finally 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine
  5. distillationwas distilled at 142°-145° C. (9 torr.) as a colourless liquid which
  6. customcrystallised
  7. custom27.23 g were obtained

Sources & evidence

ORD record
ord-88ec803e48514923b44a474a440203a1
Source dataset
uspto-grants-1994_03
Patent number
US05292886

Reaction notes

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