Ethanol → Ethyl 3-(pyridin-4-yl)acrylate

HRID 1740999Notes

Reaction equation

HRID 1740999 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 953033-(4-Pyridinyl)-2-propenoic acid

Product 1

HCID 53396309Ethyl 3-(pyridin-4-yl)acrylateYield 93%

Procedure

3-(4-Pyridyl)acrylic acid (16.18 g, 0.1085 mol) was slurried in 200 ml of absolute ethanol. Concentrated sulfuric acid (8 ml) was added and the reaction was refluxed for 3 hours. After cooling, the solvent was evaporated and the residue was cautiously neutralized with saturated sodium bicarbonate solution. The resulting mixture was then extracted twice with diethyl ether. The organic extracts were washed with water and then brine, dried over MgSO4 and concentrated to afford 17.88 g (93% yield) of the subtitle compound.

Workup

  1. temperaturethe reaction was refluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. extractionThe resulting mixture was then extracted twice with diethyl ether
  5. washThe organic extracts were washed with water
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a647f20cc4334c00b9caab2ee5ba2aaf
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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