Dichloromethane → (5-Methylpyridin-2-yl)methanol

HRID 1620801Notes

Reaction equation

HRID 1620801 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.CC1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N+:10]=1[O-].[OH-].[Na+].ClCCl>O>[CH3:15][C:12]1[CH:13]=[CH:14][C:6]([CH2:5][OH:7])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 5717732,5-Dimethylpyridin-1-ium-1-olate

Product 1

HCID 12325387(5-Methylpyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To acetic anhydride (1.61 L) at 90° C. was added 2,5-dimethyl-pyridine 1-oxide (1000 g) dropwise over 3 hours, maintaining a temperature between 90-100° C. The reaction was stirred at 90° C. for 1.5 hours, and then cooled with stirring overnight. The mixture was slowly poured into aqueous 25% sodium hydroxide (3 L) over 4 hours, and then dichloromethane (8 L) and water (8 L) were added, and the mixture was allowed to separate for 2 days. The aqueous layer was separated and extracted separately with dichloromethane and ethyl acetate, and the combined organic layers were concentrated to dryness. The crude material was applied to the top of a pad of silica (˜1 kg) and eluted with ethyl acetate until no product was observed in the eluant. The filtrate was concentrated under vacuum to give the desired product (320 g).

Workup

  1. temperaturecooled
  2. stirringwith stirring overnight
  3. customto separate for 2 days
  4. customThe aqueous layer was separated
  5. extractionextracted separately with dichloromethane and ethyl acetate
  6. concentrationthe combined organic layers were concentrated to dryness
  7. washeluted with ethyl acetate until no product
  8. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8f9a2326cd8142adb0975587f6c9282b
Source dataset
uspto-grants-2014_07
Patent number
US08772495B2

Reaction notes

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