Mesitaldehyde or mesitylaldehyde is a colorless aromatic aldehyde. It is a liquid with a characteristic odor. It is commonly used as a precursor in the synthesis of various organic compounds, including pharmaceuticals, fragrances, and dyes.
Properties
Mesitaldehyde is a derivative of
benzaldehyde, with three
Methyl group attached to the
benzene ring at positions 2, 4, and 6. This substitution with electron-donating methyl groups activates the aromatic ring for further electrophilic substitution reactions. Due to the
hydrophobicity of the methyl groups, it is less soluble in water but more soluble in organic solvents. It is stable at ordinary temperatures.
Synthesis and uses
Mesitaldehyde is synthesized through the oxidation of
mesitylene in acidic medium, typically using oxidants like chromium trioxide or potassium permanganate, followed by purification steps to isolate the aldehyde. It can also be prepared by
formylation of mesitylene by reacting Mesitylene with a formyl group source such as
paraformaldehyde or DMF (
N,
N-dimethylformamide) under specific conditions with a suitable catalyst. There are many other methods such as oxidation of acetylmesitylene by potassium permanganate, reduction of mesitoyl chloride, reaction of mesityllithum with iron pentacarbonyl, etc.
It is primarily used as an intermediate in organic synthesis for various products such as pharmaceuticals, dyes, and fragrances. Due to its reactive nature, mesitaldehyde itself isn't likely the final drug molecule in medications.
See also
