Salicylaldehyde
chemical compound
Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. It is a colorless oily liquid, with a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.
Production
Salicylaldehyde is produced by condensation of phenol with formaldehyde to give hydroxybenzyl alcohol, which is oxidized to the aldehyde.
Salicylaldehydes in general are prepared by ortho-selective formylation reactions from the corresponding phenol, for instance by the Duff reaction, Reimer–Tiemann reaction, or by treatment with paraformaldehyde in the presence of magnesium chloride and a base.
Natural occurrences
Salicylaldehyde is a characteristic aroma component of buckwheat. Salicylaldehyde also occurs in the larval defensive secretions of several leaf beetle species that belong the subtribe Chrysomelina. An example for a leaf beetle species that produces salicylaldehyde is the red poplar leaf beetle Chrysomela populi.
Reactions and applications
Salicylaldehyde is mainly used commercially as a precursor to coumarin.
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