Acetic Acid → (4-Methylpyridin-2-yl)methyl acetate

HRID 358575Notes

Reaction equation

HRID 358575 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.OO.C(=O)([O-])[O-].[Na+].[Na+].[C:17]([OH:20])(=[O:19])[CH3:18]>>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH2:1][O:20][C:17](=[O:19])[CH3:18])[CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 79362,4-DimethylpyridineHCID 10340Sodium Carbonate

Product 1

HCID 19912996(4-Methylpyridin-2-yl)methyl acetate

Procedure

24.3 ml of 2,4-dimethylpyridine were dissolved in 80 ml of glacial acetic acid, the solution was mixed with 30 ml of 30% hydrogen peroxide and refluxed for 25 hours. The solution was then adjusted to approximately pH 8 with saturated sodium carbonate solution, the solution was extracted with dichloromethane and the organic phase rotated in. The residue was mixed with 90 ml of acetic anhydride and refluxed for 1.5 hours. The pH-value of the solution was adjusted to approximately 8 with 40% NaOH and the solution was extracted with trichloromethane. 30 g of crude 4-methyl-2-acetoxymethylpyridine were obtained.

Workup

  1. temperaturerefluxed for 25 hours
  2. extractionthe solution was extracted with dichloromethane
  3. additionThe residue was mixed with 90 ml of acetic anhydride
  4. temperaturerefluxed for 1.5 hours
  5. extractionthe solution was extracted with trichloromethane

Sources & evidence

ORD record
ord-b414d92fd8af4b26852066239e7c61a7
Source dataset
uspto-grants-1991_03
Patent number
US04997835

Reaction notes

Loading…