Ethanol → Ethyl 2-dimethylaminomethylacrylate

HRID 616430Notes

Reaction equation

HRID 616430 reaction equation
[CH3:1][N:2]([CH2:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7])[CH3:3].S(=O)(=O)(O)O.[CH2:15](O)[CH3:16]>>[CH3:1][N:2]([CH2:4][C:5](=[CH2:9])[C:6]([O:8][CH2:15][CH3:16])=[O:7])[CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2235812-((Dimethylamino)methyl)prop-2-enoic acid

Product 1

HCID 20370247Ethyl 2-dimethylaminomethylacrylate

Procedure

A solution of the 2-dimethylaminomethylacrylic acid (35 g) compound prepared as in Example 1 in ethanol (350 ml) and concentrated sulphuric acid (60 ml) were boiled under reflux for three hours. The solution was evaporated to half volume and poured into water (1 liter). The aqueous solution was neutralised by the addition of solid sodium carbonate and extracted with ether. Evaporation of the ether solution gave a pale brown oil which was distilled to give a colourless oil (boiling point 84° C/20 mm). The product was identical with that obtained in Example 4.

Workup

  1. temperatureunder reflux for three hours
  2. customThe solution was evaporated to half volume
  3. additionpoured into water (1 liter)
  4. additionThe aqueous solution was neutralised by the addition of solid sodium carbonate
  5. extractionextracted with ether
  6. customEvaporation of the ether solution
  7. customgave a pale brown oil which
  8. distillationwas distilled
  9. customto give a colourless oil (boiling point 84° C/20 mm)
  10. customthat obtained in Example 4

Sources & evidence

ORD record
ord-3e6ce0bdaeae4f5cb682a9d984b4e87e
Source dataset
uspto-grants-1978_02
Patent number
US04074051

Reaction notes

Loading…