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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

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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	1.00	0.079	0.07
71-43-2 71-43-2 · C6H6	1.05	1.05	0.082	0.09

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	1.10	0.147	0.06

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	—	149.48	12.695	9.55

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	1.00	0.120	0.12

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: 0.12 g (1.00 mmol)
Expected isolated · 72–88 % yield: 0.09 – 0.11 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

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