Acetic Anhydride → (3-Methylpyridin-4-yl)methyl acetate

HRID 236451Notes

Reaction equation

HRID 236451 reaction equation
[N+:1]1([O-])[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=1.[C:10]([O:13]C(=O)C)(=[O:12])[CH3:11]>O>[C:10]([O:13][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][C:3]=1[CH3:8])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 3024543,4-Dimethylpyridine 1-oxide

Product 1

HCID 569215(3-Methylpyridin-4-yl)methyl acetateYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The N-oxide was added portionwise to 60 mL of acetic anhydride and the resulting dark orange solution was heated (water-bath) at about 90° C. for 1 h. The excess acetic anhydride was then distilled off under reduced pressure and the material boiling at 90°-120° C./0.1 torr (39.0 g) was collected. Chromatography of this oil (silica gel/ethyl acetate-pet.ether=2:3) afforded pure 4-acetoxymethyl-3-methylpyridine (19.0 g, 30%) as an oil: ir (neat) 1745 cm-1.

Workup

  1. distillationThe excess acetic anhydride was then distilled off under reduced pressure
  2. customthe material boiling at 90°-120° C./0.1 torr (39.0 g) was collected

Sources & evidence

ORD record
ord-4733ba85c7be43ba8ce4561e8017e9af
Source dataset
uspto-grants-1987_02
Patent number
US04644061

Reaction notes

Loading…