Ethanol → Ethyl 3-nitropropionate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureis refluxed overnight
- customThe reaction mixture is evaporated
- customthe residue partitioned between water and ether
- washThe ether layer is washed with water, aqueous sodium bicarbonate solution and brine
- dry with materialdried over sodium sulfate
- customThe ether is removed in vacuo
- distillationthe product distilled as a clear liquid
Sources & evidence
- ORD record
- ord-b6b6eb9d9c334d648e3638cd3c3b1943
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06638929B2
Reaction notes
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