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

HRID 486818노트

반응식

HRID 486818 반응식
[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

참가 물질

4

반응물 3

HCID 14798Sodium Hydroxide2회HCID 50672892-(Acetoxymethyl)-4-methoxy-3,5-dimethylpyridineHCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxide

생성물 1

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

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-88ec803e48514923b44a474a440203a1
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292886

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