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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.

File:SalicylaldDerivs.png
Figure. Illustrative compounds derived from salicylaldehyde. From the left: catechol, benzofuran, a salicylaldehydimine (R = alkyl or aryl), 3-carbethoxycoumarin.
References

References

  1. ↑ Dakin, H. D. “Catechol” Organic Syntheses, Collected Volume 1, p.149 (1941).http://www.orgsyn.org/orgsyn/pdfs/CV1P0149.pdf
  2. ↑ 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
  3. ↑ 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.
External links

de:Salicylaldehyd it:Aldeide salicilica

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