Ethanol → Ethyl pyridine-4-acetate

HRID 1164871Notes

Reaction equation

HRID 1164871 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:24](O)[CH3:25]>>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:24][CH3:25])=[O:9])=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 342284-Pyridineacetic acid

Product 1

HCID 736321Ethyl pyridine-4-acetate

Procedure

A solution of 4-pyridylacetic acid in 500 ml of anhydrous ethanol containing 75 ml of concentrated sulfuric acid is refluxed 18 hours. The solution is cooled to 0° an neutralized by addition of sodium hydroxide solution and saturated aqueous sodium carbonate. Extraction with ethyl acetate yields on concentration in vacuo ethyl 4-pyridylacetate.

Workup

  1. temperatureThe solution is cooled to 0°
  2. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-5e9b8b6d69f642e0a5d2f8a4b577f1c3
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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