Acetic Anhydride → 2-Pyridinemethanol, 5-methyl-, 2-acetate

HRID 2051771Notes

Reaction equation

HRID 2051771 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-].[C:10]([O:13]C(=O)C)(=[O:12])[CH3:11]>C(O)(=O)C>[C:10]([O:13][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5717732,5-Dimethylpyridin-1-ium-1-olate

Product 1

HCID 123253842-Pyridinemethanol, 5-methyl-, 2-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

11.5 g of 2,5-dimethylpyridine-N-oxide in 5 ml of acetic acid were added dropwise to 18 ml of acetic anhydride pre-heated to 120°. The reaction solution was boiled under reflux for a further 45 minutes, concentrated by evaporation on a rotary evaporator, and distilled at 8 mm Hg/115°. 14.0 g of 2-acetoxymethyl-5-methylpyridine was obtained.

Workup

  1. temperaturepre-heated to 120°
  2. temperatureunder reflux for a further 45 minutes
  3. concentrationconcentrated by evaporation on a rotary evaporator
  4. distillationdistilled at 8 mm Hg/115°

Sources & evidence

ORD record
ord-3f47da391fdb4b7e81858e0412059940
Source dataset
uspto-grants-1980_01
Patent number
US04182766

Reaction notes

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