Acetic Anhydride → 2-Acetoxymethyl-5-methoxypyridine

HRID 904148Notes

Reaction equation

HRID 904148 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[N+:7]([O-])[CH:8]=1.[C:11]([O:14]C(=O)C)(=[O:13])[CH3:12]>>[C:11]([O:14][CH2:10][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][N:7]=1)(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 122140195-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 145171522-Acetoxymethyl-5-methoxypyridine

Procedure

The crude N-oxide product obtained above (13.5 g.) was then placed in acetic anhydride (100 ml.) and heated on a steam bath for a period of three hours. The excess anhydride was thereafter removed by means of distillation and the liquid residue so obtained was fractionally distilled to give pure 2-acetoxymethyl-5-methoxypyridine (yield, 6.6 g.), b.p. 148°-150° C./12 mm. Hg. This particular product was then hydrolyzed by heating same on a steam bath while in concentrated hydrochloric acid for a period of four hours. Evaporation of the resulting reaction solution then gave crude 2-hydroxymethyl-5-methoxypyridine as the residue.

Workup

  1. temperatureheated on a steam bath for a period of three hours
  2. customThe excess anhydride was thereafter removed by means of distillation
  3. customthe liquid residue so obtained
  4. distillationwas fractionally distilled

Sources & evidence

ORD record
ord-d207bd5aca9046519a8e9827553bcd71
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

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