The Henry reaction uses a catalytic base to convert a nitroalkane and a ketone or aldehyde to a β-nitro alcohol. The base abstracts an α-proton from nitroalkane, producing a resonance stabilized anion, which attacks the carbonyl, to form a β-nitro alkoxide that is protonated by the base’s conjugate acid. β-nitro alcohols can be converted to nitroalkenes, α-nitro ketones, or β-amino alcohols via dehydration, oxidation, and reduction respectively.

• Reagents: Catalytic Base (Alkali Metal Hydroxide, Alkoxide, Carbonate, KF, Transition Metal Complex, Amine, DBU, etc.), Solvent
• Reactant: Nitroalkane with α-Hydrogen, Aryl/Aliphatic Aldehyde or Ketone
• Product: β-Nitro Alcohol
• Type of Reaction: Nitro-Aldol Condensation
• Bond Formation: C-C

Mechanism

Original Paper

Top Citations

Related Reactions

Related Compounds