--- title: "Dakin oxidation Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/dakin-oxidation/ description: "Dakin oxidation template: Hydroperoxide adds to the C=O of salicylaldehyde; the electron-rich aryl group migrates to oxygen as hydroxide leaves (as in the…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Dakin oxidation [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Dakin oxidation template ![Dakin oxidation template: Hydroperoxide adds to the C=O of salicylaldehyde; the electron-rich aryl group migrates to oxygen as hydroxide leaves (as in the Baeyer–Villiger), and the aryl formate is hydrolysed to catechol.](https://www.moldraw.com/templates/dakin-oxidation.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). Hydroperoxide adds to the C=O of salicylaldehyde; the electron-rich aryl group migrates to oxygen as hydroxide leaves (as in the Baeyer–Villiger), and the aryl formate is hydrolysed to catechol. ## Mechanism step by step Alkaline H₂O₂ turns an o- or p-hydroxybenzaldehyde into a benzenediol and formate 1. **Hydroperoxide adds** – HOO⁻ (from H₂O₂ and NaOH) adds to the C=O: a tetrahedral intermediate 2. **Aryl migration (slow)** – The C=O reforms, the aryl group moves to O and hydroxide leaves: an aryl formate 3. **Hydroxide adds to the ester** – Ester hydrolysis begins: a second tetrahedral intermediate 4. **Phenoxide leaves** – Collapse releases the phenoxide and formic acid (formate in base); acid work-up gives catechol ## Key points - Needs an electron-donating OH (or NH₂) ortho or para to the CHO: p-hydroxybenzaldehyde gives hydroquinone, salicylaldehyde gives catechol. - The migration step is the Baeyer–Villiger step: the electron-rich aryl group (helped by the phenoxide in base) migrates in preference to H. - With no donor, or a donor meta to the CHO, H migrates instead and the product is the benzoic acid. - Mild and cheap (H₂O₂, NaOH, or sodium percarbonate): a route to phenols from aldehydes. Drawn with 108 atoms, 14 arrows, 8 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 Dakin oxidation template free? You can preview the Dakin oxidation 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 Dakin oxidation 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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