Henry reaction

Also known as: Henry nitroaldol reaction

Schematic of the Henry reaction. Reagents: nitroalkane with alpha-hydrogen, aldehyde, ketone, base catalyst. Product: beta-nitro alcohol.

The Henry reaction is an organic reaction used to convert a nitroalkane with an α-hydrogen and an aldehyde or ketone to a β-nitro alcohol using a base catalyst. The mechanism begins with deprotonation of the nitroalkane by the base to give a resonance stabilize anionic intermediate which subsequently attacks the carbonyl compound to form an alkoxide. The alkoxide then picks up a proton from the conjugate acid of the base (H2O in this case) to give the final β-nitro alcohol product and regenerate the base catalyst.[1]


Mechanism of the Henry reaction.


Henry, L. Compt. Rend. 1895, 120, 1268