Acetic Anhydride → 2-Acetoxymethyl-3,4-dimethoxypyridine

HRID 1789054Notes

Reaction equation

HRID 1789054 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[N+:5]([O-])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:16][CH2:12][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=[CH:6][N:5]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 107496473,4-Dimethoxy-2-methyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 106085512-Acetoxymethyl-3,4-dimethoxypyridineYield 90%

Procedure

4.8 g (28 mmol) of 3,4-dimethoxy-2-methylpyridine 1-oxide are metered into 25 ml of acetic anhydride at 85° C. in the course of one hour, the mixture is stirred at the same temperature for one hour and concentrated completely in vacuo and the brown oily residue is distilled in a bulb type still under 1 Pa. 5.3 g (90% of theory) of 2-acetoxymethyl-3,4-dimethoxypyridine are obtained; b.p. 125°-130° C.

Workup

  1. concentrationconcentrated completely in vacuo
  2. distillationthe brown oily residue is distilled in a bulb type still under 1 Pa

Sources & evidence

ORD record
ord-c54f61d1844b40efaf008bcca8fff9bf
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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