Ethanol → Ethyl 3-nitropropionic acid

HRID 408446Notes

Reaction equation

HRID 408446 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:14](O)[CH3:15]>>[CH2:14]([CH:5]([CH2:4][N+:1]([O-:3])=[O:2])[C:6]([OH:8])=[O:7])[CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 16783-Nitropropionic acid

Product 1

HCID 86703358Ethyl 3-nitropropionic acid

Procedure

To a solution of 2 gr of 3-nitropropionic acid (41) in 30 mL of ethanol add catalytic amount of concentrated sulphuric acid (0.8 mL) and reflux overnight. Then add water and extracted with ethylacetate. The organic layer was washed with saturated sodium bicarbonate solution, saturated sodium chloride and water. Purification from column gives ethyl 3-nitropropionic acid (26) as pale yellow liquid with boiling point 92° C. at 2.5 torr.

Workup

  1. temperaturereflux overnight
  2. extractionThen add water and extracted with ethylacetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution, saturated sodium chloride and water
  4. customPurification from column

Sources & evidence

ORD record
ord-5550a87ede2a43dfb5d94e8070cc45ac
Source dataset
uspto-grants-2014_06
Patent number
US08759339B2

Reaction notes

Loading…