Ethanol → Ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate

HRID 1247894Notes

Reaction equation

HRID 1247894 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([O:12][CH2:18][CH3:19])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 541408533-(6-Methyl-3-pyridyl)acrylic acid

Product 1

HCID 54365744Ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate

Procedure

A stirred mixture of 3-(6-methyl-3-pyridyl)acrylic acid (50.70 g), dry ethanol (350 ml) and concentrated sulphuric acid (25 ml) was heated under reflux for 18 hours and ethanol (~250 ml) was removed by evaporation. The residue was poured into ice-aqueous ammonia and the mixture was extracted with ether. The ether extracts were washed with water and evaporated to an oil which crystallised on standing to give ethyl 3-(6-methyl-3-pyridyl)acrylate m.p. 36°-37°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customethanol (~250 ml) was removed by evaporation
  4. additionThe residue was poured into ice-aqueous ammonia
  5. extractionthe mixture was extracted with ether
  6. washThe ether extracts were washed with water
  7. customevaporated to an oil which
  8. customcrystallised

Sources & evidence

ORD record
ord-8e1e39793af24028921cf7821ac3cf06
Source dataset
uspto-grants-1985_06
Patent number
US04521418

Reaction notes

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