Acetic Anhydride → (4-methoxypyridin-2-yl)methyl Acetate

HRID 638585Notes

Reaction equation

HRID 638585 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N+:3]=1[O-].[C:11]([O:14]C(=O)C)(=[O:13])[CH3:12]>>[C:11]([O:14][CH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1)(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 107018932-Methyl-4-methoxypyridine-N-oxide

Product 1

HCID 10726082(4-methoxypyridin-2-yl)methyl AcetateYield 78%

Procedure

To 2-methyl-4-methoxypyridine-N-oxide (23 g, 0.165 mole) in a 1 liter wide necked flask fitted with a large condenser was added ice-cool acetic anhydride (35 ml, 0.37 mole) with stirring. The mixture was allowed to warm to room temperature whereupon a vigorous exothermic reaction occurred. The dark mixture was stirred for 1 hour before evaporating the excess acetic anhydride and distilling the residue to give the title compound (23.26 g, 78%), b.p. 125° C. at 0.1 mm mercury.

Workup

  1. additionwas added ice-
  2. stirringThe dark mixture was stirred for 1 hour
  3. custombefore evaporating the excess acetic anhydride
  4. distillationdistilling the residue

Sources & evidence

ORD record
ord-6d07a02efff84b10b9246d400a1d5d35
Source dataset
uspto-grants-1985_12
Patent number
US04562197

Reaction notes

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