Tools · Synthesis

Reaction Scale Calculator

Pick a stored reaction, fix one reagent's amount, get every other reagent's quantity by stoichiometric equivalents. Solvent volume derived from your substrate concentration. Densities + molar masses come from our molecule database.

Switch reaction

Press / to jump here from anywhere. Type to search all 3374 reactions.

Friedel-Crafts acylation: benzene + acetyl chloride → acetophenone

PhH + CH3–C(=O)–Cl → Ph–C(=O)–CH3 + HCl

Textbook electrophilic aromatic substitution via the AlCl3-generated acylium ion. The product ketone (acetophenone) deactivates the ring toward further acylation, so unlike F-C alkylation, monoacylation is clean — no polyacylation problem. AlCl3 is used at 1.1 equiv (not catalytic) because it complexes the product 1:1; aqueous acidic workup decomposes the complex to free the ketone.

Conditions: Suspend AlCl3 (1.1 equiv) in dry CH2Cl2 (~3 mL per mmol acetyl chloride) under N2. Cool to 0 °C; add acetyl chloride (1.0 equiv, slowly via syringe — exotherm!). The mixture turns yellow-brown as the AlCl3-AcCl complex forms. Add benzene (1.05 equiv, slight excess) dropwise over 10 min keeping T < 5 °C. Warm to RT; stir 1–4 h until HCl evolution ceases. Workup — Cautiously pour onto crushed ice; separate organic; wash with sat. NaHCO3 (decomposes residual AlCl3 complex), water, brine; dry MgSO4; concentrate. Distil at reduced pressure (bp 202 °C at 760 mmHg, or ~80 °C at 10 mmHg). Pure acetophenone is a colourless liquid with a sweet almond-like odour.

Expected yield: 72–88 %
Expected duration: 1–4 h at RT after 0 °C addition; HCl evolution is the endpoint signal

Mechanism reference ↗

Anchor reagent — fix this amount, scale everything else Substrate concentration · M

Amount r Unit

Updates as you type · the URL captures every input.

Reactants

Reactants for Friedel-Crafts acylation: benzene + acetyl chloride → acetophenone: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
Acetyl Chloride 75-36-5 · C2H3ClO	1.0	9.09	0.714	0.64
71-43-2 71-43-2 · C6H6	1.05	9.55	0.746	0.85

Catalyst

Catalyst for Friedel-Crafts acylation: benzene + acetyl chloride → acetophenone: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
Aluminium Chloride 7446-70-0 · AlCl3	1.1	10.00	1.333	0.54

Solvent

Solvent for Friedel-Crafts acylation: benzene + acetyl chloride → acetophenone: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
Dichloromethane SDS 75-09-2 · CH2Cl2	—	1358.92	115.413	86.78

Product

Product for Friedel-Crafts acylation: benzene + acetyl chloride → acetophenone: stoichiometric quantities derived from the anchor amount.
Reagent	Equiv	Moles · mmol	Mass · g	Volume · mL
Acetophenone 98-86-2 · C8H8O	1.0	9.09	1.092	1.06

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: Acetophenone 98-86-2 · C8H8O
Theoretical max: 1.09 g (9.09 mmol)
Expected isolated · 72–88 % yield: 0.79 – 0.96 g

Stoichiometry: moles_X = (moles_anchor / equiv_anchor) × equiv_X. Mass = moles × MW; volume = mass / ρ. Solvent volume = total reactant moles ÷ substrate concentration.

Catalytic Intramolecular Friedel-Crafts Reaction of Benzyl Meldrum's Acid Derivatives: Preparation of 5,6-Dimethoxy-2-Methyl-1-Indanone Electrophilic aromatic substitution

Related chemistry tools

Stoichiometry Calculator Limiting reagent, theoretical yield, and reaction quantities with full unit propagation. Molar Mass Calculator Molecular weight and percent composition to weigh out each reagent. Chemical Equation Balancer Balance the reaction before you scale it. Fractional Distillation Predictor Plan the work-up — predict which fractions distil and where azeotropes bite.