Ethanol → Ethyl 3-nitropropionate

HRID 2213798Notes

Reaction equation

HRID 2213798 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH2:9](O)[CH3:10]>S(=O)(=O)(O)O>[N+:1]([CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 16783-Nitropropionic acid

Product 1

HCID 11804910Ethyl 3-nitropropionateYield 69%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 25 g (0.21 mole) of 3-nitropropionic acid, 300 mL of absolute ethanol and 10 drops of concentrated sulfuric acid is refluxed overnight. The reaction mixture is evaporated, and the residue partitioned between water and ether. The ether layer is washed with water, aqueous sodium bicarbonate solution and brine, then dried over sodium sulfate. The ether is removed in vacuo and the product distilled as a clear liquid to provide 21.54 g (69%) of Ethyl 3-nitropropionate as a clear oil, b.p. 160–165° C. at 120 mm Hg.

Workup

  1. temperatureis refluxed overnight
  2. customThe reaction mixture is evaporated
  3. customthe residue partitioned between water and ether
  4. washThe ether layer is washed with water, aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. customThe ether is removed in vacuo
  7. distillationthe product distilled as a clear liquid

Sources & evidence

ORD record
ord-9c0ad8e205484f1ea9dbf4fea585aca2
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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