Henry reaction (nitroaldol addition)

Reagent table at any scale. Enter how much benzaldehyde you have, or pick another reagent, and every mass, volume and amount follows.

Conditions and workup
OBenzaldehyde+N+OO−Nitromethanen-BuNH2 (10 mol%)AcOHON+O−β-Nitrostyrene70–80 %
OBenzaldehyde+N+OO−Nitromethanen-BuNH2 (10 mol%)AcOHON+O−β-Nitrostyrene70–80 %

Reagent table

ReagentRoleEquivMW (g/mol)ρ (g/mL)nmV
Benzaldehyde100-52-7limitingyour amount reactant 106.12 1.050 10.0 mmol 1.06 g 1.01 mL
Nitromethane75-52-5limiting reactant 61.04 1.130 10.0 mmol 610 mg 540 µL
n-Butylamine109-73-9 catalyst10 mol% 73.14 0.730 1.00 mmol 73.1 mg 100 µL
Acetic acid64-19-7 solvent — 60.05 1.040 — — 10.0 mL
β-Nitrostyrene102-96-5 product — 149.15 — 10.0 mmol 1.49 g —
Theoretical yield1.49 g10.0 mmol of β-nitrostyrene
Expected at 70–80 %1.04 g – 1.19 gtypical isolated yield
Solvent10.0 mLAcetic acid, 1 M
Limiting reagentBenzaldehyde, Nitromethane
Notes on the reagents
Benzaldehyde
Aldehyde acceptor.
Nitromethane
Nitroalkane — limiting reagent in this template.
n-Butylamine
Primary amine catalyst — typically 5–20 mol%.
Acetic acid
Glacial acetic acid — proton shuttle + Mannich buffer.
β-Nitrostyrene
(E)-β-Nitrostyrene. Yellow crystalline needles, mp 58 °C; recrystallises cleanly from boiling EtOH or MeOH. The parent Knoevenagel-Henry condensation product — Worrall's Org. Synth. 1929 prep is the classical undergraduate preparation of this compound.
How the amounts are calculated

The amount you enter is converted to millimoles with the molar mass, or with density and molar mass for a volume. Dividing by its equivalents gives the millimoles per equivalent; every other reagent is that times its own equivalents. Masses use the molar mass of the structure. Volumes are given for compounds that are liquid at room temperature and have a density on file. A reagent sold as a solution, such as n-BuLi in hexanes, gets the volume of that solution; enter your bottle's titre and every volume follows.

The theoretical yield assumes full conversion of the limiting reagent: the reactant with the fewest millimoles per stoichiometric coefficient. Change an equivalent and the limiting reagent may change with it.

Solvent volume and concentration

The concentration refers to the substrate, the limiting reagent: solvent volume = millimoles of substrate ÷ concentration, since 1 M is 1 mmol/mL. Liquid reagents add to the final volume, so the real concentration ends up slightly lower. Leave the field empty to leave the solvent out.

What the table cannot know

Purity, water content and reagents sold as solutions. Grignard reagents and organolithiums are bought as solutions: take the millimoles from the table and divide by the molarity on the bottle to get the volume to syringe out.

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