Mitsunobu reaction: benzyl alcohol + phthalimide → N-benzyl phthalimide
Reagent table at any scale. Enter how much benzyl alcohol you have, or pick another reagent, and every mass, volume and amount follows.
Notes on the reagents
- Benzyl alcohol
- Benzyl alcohol — primary alcohol; SN2 happens with inversion at this carbon.
- Phthalimide
- Phthalimide — acidic NH (pKa ~8.3), comfortably below the Mitsunobu's ~13 pKa cutoff. Slight excess to compensate for incomplete deprotonation.
- Diisopropyl azodicarboxylate
- Diisopropyl azodicarboxylate (DIAD) — stoichiometric oxidant; reduced to the corresponding hydrazine. Add slowly at 0 °C; explosive on heating.
- Triphenylphosphine
- Triphenylphosphine — stoichiometric reductant; oxidised to PPh3=O.
- Tetrahydrofuran
- Dry THF — standard Mitsunobu solvent. Use freshly distilled or recently-opened anhydrous bottle; trace water deactivates the betaine intermediate.
- Benzylphthalimide
- N-Benzyl phthalimide — white crystalline; mp 116 °C; recrystallises from EtOH. Hydrolyse with hydrazine in EtOH to liberate benzylamine (Gabriel synthesis).
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.