Friedel-Crafts acylation: benzene + acetyl chloride → acetophenone

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

Conditions and workup
OClAcetyl chloride+BenzeneAlCl3 (1.1 equiv)CH2Cl2OAcetophenone72–88 %
OClAcetyl chloride+BenzeneAlCl3 (1.1 equiv)CH2Cl2OAcetophenone72–88 %

Reagent table

ReagentRoleEquivMW (g/mol)ρ (g/mL)nmV
Acetyl chloride75-36-5limitingyour amount reactant 78.50 1.110 12.7 mmol 1.00 g 901 µL
Benzene71-43-2 reactant 78.11 0.880 13.4 mmol 1.04 g 1.19 mL
Aluminium chloride7446-70-0 reagent 133.33 — 14.0 mmol 1.87 g —
Dichloromethane75-09-2 solvent — 84.93 1.330 — — 38.6 mL
Acetophenone98-86-2 product — 120.15 1.030 12.7 mmol 1.53 g —
Theoretical yield1.53 g12.7 mmol of acetophenone
Expected at 72–88 %1.10 g – 1.35 gtypical isolated yield
Solvent38.6 mLDichloromethane, 0.33 M
Limiting reagentAcetyl chloride
Notes on the reagents
Acetyl chloride
Acetyl chloride — limiting reagent. Moisture-sensitive (hydrolyses to acetic acid + HCl); transfer by syringe under N2. Stench is characteristic — work in a hood.
Benzene
Benzene — slight excess; suppresses polyacylation (already kinetically disfavoured by ring deactivation, but excess locks this in). Carcinogen — strict hood discipline.
Aluminium chloride
Aluminum chloride (anhydrous) — Lewis acid. Listed at 1.1 equiv rather than catalytic because the ketone product complexes the AlCl3 1:1; stoichiometric load is needed to keep free AlCl3 available for the next turnover. Aqueous workup decomposes the complex.
Dichloromethane
Dichloromethane — anhydrous. Chlorobenzene (108-90-7) and carbon disulfide (also classic) are alternatives but DCM is the modern bench standard. Excludes water — AlCl3 reacts violently with H2O.
Acetophenone
Acetophenone — colourless liquid, bp 202 °C; sweet almond/hawthorn-like odour. Used industrially as a fragrance ingredient and pharmaceutical intermediate (e.g. ephedrine 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.

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