Salicylaldehyde

This colorless oily liquid has a bitter almond odor at higher concentration.

Salicylaldehyde is produced by condensation of phenol with formaldehyde to give hydroxybenzyl alcohol, which is oxidized to the aldehyde.

[7] Salicylaldehyde also occurs in the larval defensive secretions of several leaf beetle species that belong the subtribe Chrysomelina.

When the aldehyde is reacted with an amine to form an imine, the internal hydrogen bond is even stronger.

[17] The internal hydrogen bond also ensures that the aldehyde (or corresponding imine) is held into the same plane, making the whole molecule essentially flat.

Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Catechol , benzofuran , a salicylaldehydimine (R = alkyl or aryl), 3-carbethoxycoumarin