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Reliable, easy-to-read patient information on common medical conditions — written in plain language, free of jargon, and grounded in current evidence. Browse the most frequent diagnoses, understand what they mean for everyday life, and learn which steps and questions help you have a focused conversation with your doctor.
Salicylaldehyde
Introduction
Salicylaldehyde, or 2-hydroxybenzaldehyde, is the chemical compound with the formula C6H4CHO-2-OH. This colourless oily liquid has a bitter almond odor. Salicylaldehyde is a key precursor to a variety chelating agents, some of which are commercially important. It can be prepared from phenol and chloroform by heating with sodium hydroxide in a Reimer-Tiemann reaction.
Salicylaldehyde is a common highly functionalized arene that has often been exploited as a precursor to still other chemicals, which are shown in the figure.
- Salicylaldehyde is converted to chelating ligands via condensation with amines. With ethylenediamine, it condenses to give the popular diprotic ligand H2salen. Hydroxylamine gives salicylaldoxime.
- oxidation with hydrogen peroxide gives catechol (1,2-dihydroxybenzene).[1]
- condensation with diethyl malonate gives a derivative of the heterocycle coumarin.[2]
- etherification with chloroacetic acid followed by cyclisation gives the heterocycle benzofuran.[3]
References
References
- ↑ Dakin, H. D. “Catechol” Organic Syntheses, Collected Volume 1, p.149 (1941).http://www.orgsyn.org/orgsyn/pdfs/CV1P0149.pdf
- ↑ Horning, E. C.; Horning, M. G.; Dimmig, D. A. “3-Carbethoxycoumarin” Organic Syntheses, Collected Volume 3, p.165 (1955).http://www.orgsyn.org/orgsyn/pdfs/CV3P0165.pdf
- ↑ Burgstahler, A. W.; Worden, L. R. “Coumarone” Organic Syntheses, Collected Volume 5, p.251 (1973).http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf
General reading
General reading
- Merck Index, 11th Edition, 8295.
