--- title: "Reimer–Tiemann reaction Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/reimer-tiemann/ description: "Reimer–Tiemann reaction template: Base turns CHCl₃ into :CCl₂, phenoxide attacks it at the ortho carbon and hydrolysis of the CHCl₂ group gives…" 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/) › Reimer–Tiemann reaction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Reimer–Tiemann reaction template ![Reimer–Tiemann reaction template: Base turns CHCl₃ into :CCl₂, phenoxide attacks it at the ortho carbon and hydrolysis of the CHCl₂ group gives salicylaldehyde.](https://www.moldraw.com/templates/reimer-tiemann.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). Base turns CHCl₃ into :CCl₂, phenoxide attacks it at the ortho carbon and hydrolysis of the CHCl₂ group gives salicylaldehyde. ## Mechanism step by step Dichlorocarbene from chloroform formylates a phenoxide at the ortho position 1. **Dichlorocarbene** – NaOH deprotonates CHCl₃; CCl₃⁻ then loses Cl⁻ 2. **Attack on the carbene** – The ortho carbon of phenoxide attacks 3. **Tautomerisation** – Proton transfer restores the aromatic ring ## Key points - First, hydroxide removes the C–H proton of chloroform to give CCl₃⁻. - Hydroxide then hydrolyses the CHCl₂ group to CHO; acid work-up gives salicylaldehyde. - Ortho attack dominates; some para product forms. - Dichlorocarbene is an electron-poor (singlet) carbene: a lone pair and an empty orbital. - With CCl₄ instead of CHCl₃ the same route gives salicylic acid. Drawn with 65 atoms, 10 arrows, 5 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 Reimer–Tiemann reaction template free? You can preview the Reimer–Tiemann reaction 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 Reimer–Tiemann reaction 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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