Nitric Acid → Ethyl nitroacetate

HRID 373355Notes

Reaction equation

HRID 373355 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2]C(C)=O.[N+:10]([O-])([OH:12])=[O:11]>C(OC(=O)C)(=O)C>[N+:10]([CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 8868Ethyl Acetoacetate

Product 1

HCID 69379Ethyl nitroacetate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Another route was disclosed by early researchers Bouveault and Wahl, Bull. Soc. Chim. France, 31, 847-54 (1904), whereby ethyl acetoacetate was reacted with absolute nitric acid in acetic anhydride at 30°-35° C., but low yields of ethyl nitroacetate were reported. This work was later confirmed by Arndt and Rose in J. Chem. Soc. 1935, 1-10. The major product produced using the conditions of Bouveault and Wahl was found to be diethyl2-oxofurazan dicarboxylate.

Sources & evidence

ORD record
ord-dab4f7c84a1646d0a19f1872afa404bf
Source dataset
uspto-grants-1992_11
Patent number
US05162572

Reaction notes

Loading…