Sulfuric Acid → (2-Methylpyridin-4-yl)methanol

HRID 1860388Notes

Reaction equation

HRID 1860388 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.S(=O)(=O)(O)O.[OH2:25].[CH3:26]O>>[OH:25][CH2:26][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([CH3:13])[CH:19]=1

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 79752-MethylpyridineHCID 62648Ammonium Persulfate2×HCID 22242641Methanol--water (1/1)

Product 1

HCID 9942144(2-Methylpyridin-4-yl)methanol

Procedure

Ammonium persulfate (231 g) was added to a solution of 2-methylpyridine (100 ml) in water-MeOH (350:700 ml); and then concentrated sulfuric acid (58 m,) was added. The mixture was stirred at reflux for 3 days. In this time other ammonium persulfate (20 g) and concentrated sulfuric acid (15 ml) were added. The mixture was quenched with NaOH 10% and extracted with EE (3×100 ml) and EA (3×100 ml), then the organic extracts were washed with brine (200 ml), dried and concentrated in vacuo to a yellow oil which was purified by flash chromatography (eluting with EE-EA 1:1) to give the title compound as a white solid (12.0 g).

Workup

  1. temperatureat reflux for 3 days
  2. customThe mixture was quenched with NaOH 10%
  3. extractionextracted with EE (3×100 ml) and EA (3×100 ml)
  4. washthe organic extracts were washed with brine (200 ml)
  5. customdried
  6. concentrationconcentrated in vacuo to a yellow oil which
  7. customwas purified by flash chromatography (eluting with EE-EA 1:1)

Sources & evidence

ORD record
ord-a53624594539421c8bdf8b093cf8f185
Source dataset
uspto-grants-2003_03
Patent number
US06531466B2

Reaction notes

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