Ethanol → Ethyl 2-dimethylaminomethylacrylate

HRID 616434Notes

Reaction equation

HRID 616434 reaction equation
[CH3:1][N:2]([CH2:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7])[CH3:3].[CH2:10](O)[CH3:11]>S(=O)(=O)(O)O>[CH3:1][N:2]([CH2:4][C:5](=[CH2:9])[C:6]([O:8][CH2:10][CH3:11])=[O:7])[CH3:3]

Participants

4

Reactant 2

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

Product 1

HCID 20370247Ethyl 2-dimethylaminomethylacrylateYield 55%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-dimethylaminomethylacrylic acid (129g) in concentrated sulphuric acid (105 ml, 98%) and ethanol (500 ml) was boiled under reflux for 3 hours. After evaporating to half volume and pouring the residue into water (1 liter), anhydrous sodium carbonate (212g) was added and the solution was allowed to stand for 3 hours, when it gave a neutral reaction. The aqueous mixture was extracted with ether (3 × 250 ml), after drying over anhydrous sodium sulphate, the ether extract was evaporated at atmospheric pressure. The residual pale yellow oil was distilled under reduced pressure to give ethyl 2-dimethylaminomethylacrylate (86g, 55% boiling point 84° C/20 mm).

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter evaporating to half volume
  3. additionpouring the residue into water (1 liter), anhydrous sodium carbonate (212g)
  4. additionwas added
  5. customwhen it gave
  6. customa neutral reaction
  7. extractionThe aqueous mixture was extracted with ether (3 × 250 ml)
  8. dry with materialafter drying over anhydrous sodium sulphate
  9. extractionthe ether extract
  10. customwas evaporated at atmospheric pressure
  11. distillationThe residual pale yellow oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-0f51147892774f83bb0e5aca47167dc0
Source dataset
uspto-grants-1978_02
Patent number
US04074051

Reaction notes

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