--- title: "Fries rearrangement Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/fries-rearrangement/ description: "Fries rearrangement template: AlCl₃ binds the ester oxygen of phenyl acetate and releases an acylium ion, which acylates the aluminium phenoxide at the para…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Fries rearrangement [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Fries rearrangement template ![Fries rearrangement template: AlCl₃ binds the ester oxygen of phenyl acetate and releases an acylium ion, which acylates the aluminium phenoxide at the para (or ortho) carbon; acid work-up frees the phenol.](https://www.moldraw.com/templates/fries-rearrangement.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). AlCl₃ binds the ester oxygen of phenyl acetate and releases an acylium ion, which acylates the aluminium phenoxide at the para (or ortho) carbon; acid work-up frees the phenol. ## Mechanism step by step AlCl₃ moves the acyl group of a phenyl ester onto the ring: hydroxyaryl ketones 1. **Lewis acid complex** – AlCl₃ binds the ester (phenolic) oxygen 2. **Acylium ion** – The C–O bond breaks: acylium ion and aluminium phenoxide 3. **Electrophilic attack** – The O lone pair pushes the ring onto the acylium ion (para) 4. **Deprotonation** – Loss of H⁺ restores aromaticity 5. **Work-up** – Acid breaks the O–Al bond and frees the phenol ## Key points - AlCl₃ first binds the more basic C=O oxygen and moves to the phenolic oxygen; the drawing starts from there. - Low temperature (below about 60 °C) favours the para product; high temperature (above about 160 °C) favours ortho, held as a stable Al chelate. - Crossover experiments show the acylium ion can move between molecules (intermolecular). - Photo-Fries: UV light does the same rearrangement by a radical pathway. Drawn with 176 atoms, 17 arrows, 10 shapes – every one editable in MolDraw. ## Sources - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005](https://openlibrary.org/isbn/9780124297852) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020](https://openlibrary.org/isbn/9781119371809) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Fries rearrangement template free? You can preview the Fries rearrangement template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates. ### Can I edit the Fries rearrangement template? Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it. ### Is the chemistry checked? Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page. ### Which name reactions are included? 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