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Grignard addition: phenylmagnesium bromide + benzaldehyde → diphenylmethanol
PhMgBr + Ph–CHO → [Ph2CH–OMgBr] →(H3O+) Ph2CH–OH
Textbook Grignard addition. Phenylmagnesium bromide (PhMgBr) attacks benzaldehyde's carbonyl carbon; aqueous acidic workup releases diphenylmethanol (benzhydrol). PhMgBr is bought as a 1 M or 3 M solution in anhydrous Et2O or THF — solid Grignards are not weighed. Reaction is run under N2 with rigorous water exclusion.
Conditions: Cool a flame-dried, N2-flushed flask to 0 °C. Charge anhydrous Et2O (~3 mL per mmol of benzaldehyde). Add benzaldehyde (1.0 equiv) by syringe; stir 5 min. Add PhMgBr (1.1 equiv, 1 M or 3 M solution in Et2O) dropwise over 10 min — exotherm; control addition rate to keep T < 5 °C. Warm to RT, stir 1–2 h. Workup — Quench cautiously with sat. NH4Cl (or 10 % HCl); extract with Et2O; wash organic with sat. NaHCO3 + brine; dry MgSO4. Concentrate. Recrystallise from hexane or hexane/EtOAc. White crystals; mp 65–67 °C.
- Expected yield
- 75–92 %
- Expected duration
- 1–2 h at RT after 0 °C addition
Computed quantities
Reactants
| Reagent | Equiv | Moles · mmol | Mass · g | Volume · mL |
|---|---|---|---|---|
|
Phenylmagnesium Bromide
100-58-3 · C6H5BrMg
density unavailable — volume not calculable. |
1.1 | 11.00 | 1.995 | — |
|
Benzaldehyde
100-52-7 · C7H6O
|
1.0 | 10.00 | 1.061 | 1.01 |
Solvent
| Reagent | Equiv | Moles · mmol | Mass · g | Volume · mL |
|---|---|---|---|---|
|
60-29-7
60-29-7 · C4H10O
|
— | 609.58 | 45.182 | 63.64 |
Product
| Reagent | Equiv | Moles · mmol | Mass · g | Volume · mL |
|---|---|---|---|---|
|
91-01-0
91-01-0 · C13H12O
density unavailable — volume not calculable. |
1.0 | 10.00 | 1.842 | — |
Expected isolated yield
What you should actually weigh out of the recrystallisation flask, scaled from the limiting reactant via the canonical-procedure yield window.
- Product
- 91-01-0 91-01-0 · C13H12O
- Theoretical max
- 1.84 g (10.00 mmol)
- Expected isolated · 75–92 % yield
- 1.38 – 1.70 g
Stoichiometry: moles_X = (moles_anchor / equiv_anchor) × equiv_X.
Mass = moles × MW; volume = mass / ρ. Solvent volume = total reactant moles ÷ substrate concentration.
More Organometallic addition reactions
- ALDEHYDES FROM 4,4-DIMETHYL-2-OXAZOLINE AND GRIGNARD REAGENTS: o-ANISALDEHYDE (Benzaldehyde, 2-methoxy-) Organometallic addition
- Barbier reaction Organometallic addition
- Barbier–Wieland degradation Organometallic addition
- Cross-Coupling of Alkenyl/Aryl Carboxylates with Grignard Reagents via Fe-Catalyzed C-O Bond Activation Organometallic addition
- FORMYL TRANSFER TO GRIGNARD REAGENTS WITH N-FORMYLPIPERIDINE: 3-PHENYLPROPIONALDEHYDE Organometallic addition
- Grignard reaction Organometallic addition
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