Potassium Hydroxide → Ethyl Acetate

HRID 636649

Reaction equation

HRID 636649 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][N:6]=1)(=[O:3])[CH3:2].[OH-].[K+]>CO>[OH:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][N:6]=1.[C:1]([O:4][CH2:5][CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 212552792-Acetoxy-methyl-5-methoxy-pyridine

Product 2

HCID 8857Ethyl AcetateYield 197.9%HCID 178493791HCID 178493791, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-acetoxy-methyl-5-methoxy-pyridine (1.41 g, 7.8 mmol) in methanol (30 mL) was added excess potassium hydroxide (1.6 g), and the mixture was refluxed for 2 hours. The solvent was removed in vacuo, and the residue was purified by column chromatography eluting with a heptane to ethyl acetate gradient. The extremely volatile 2-hydroxy-methyl-5-methoxy-pyridine was obtained as a solution in ethyl acetate (0.68 g, 63% yield).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography
  4. washeluting with a heptane to ethyl acetate gradient

Sources & evidence

ORD record
ord-6086957bf3ce42eebbefa4455152d51b
Source dataset
uspto-grants-2001_02
Patent number
US06194437B1

Linked notes

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