4-Methoxyphenylacetaldehyde

The Uses of 4-Methoxyphenylacetaldehyde

4-Methoxyphenylacetaldehyde is used in perfume compositions as part of the floral theme, mainly in Lilac, Heliotrope, Wallflower, Acacia, New Mown Hay, Hawthorne, and also in Fougeres as a sweetener or modifier for Anisaldehyde, etc. It blends excellently with the conventional sweeteners and florals, and produces softer, less harsh notes than Anisaldehyde or the substituted Acetophenones. The aldehyde tends to polymerize on storage and should be kept at uniform temperature, preferably in dilution, protected from daylight and air. Polymerization causes increase in viscosity and loss of odor.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 7499, 1990 DOI: 10.1016/S0040-4039(00)88528-7

Synthesis

Prod.:
1) from para-Methoxy allyl benzene with Mercuric oxide plus Iodine.
2) from pmw-Styrylcarbamic ester by hydrolysis with Sulfuric acid.
3) from Anisaldehyde via Darzens' synthesis.
4) It has also been prepared from Estragole.