p-Methylphenylacetaldehyde

Chemical properties

p-Tolylacetaldehyde has a powerful and refreshing green-fruity, "forest-like", sweet, floral odor of moderate tenacity. The undiluted material has a rather sharp initial odor, but sweetness predominates in the diluted product. The taste is sweet-fruity, mildly green at concentrations near 10 ppm.

The Uses of p-Methylphenylacetaldehyde

4-Methylphenylacetaldehyde (p-Tolylacetaldehyde) is used in perfumes, e.g., in soap, in tobacco fragrances, in the preparation of pesticides, etc.

Preparation

From p-methylbenzaldehyde; also from p-methylbenzyl chloride and hexamethylene tetramine.The methods of preparation correspond closely to those of phenylacetaldehyde. Thus, the compound can be prepared by glycidic ester synthesis from 4-methylbenzaldehyde and chloroacetate ester, by hydroformylation of 4-methylbenzylhalide with Co₂(CO)₈Na₂CO₃ in acetonitrile, or by oxidation of 4-methylstyrene.

Definition

ChEBI: (4-Methylphenyl)acetaldehyde is a member of phenylacetaldehydes.

Production Methods

p-Tolylacetaldehyde can be produced 1) from para-Methylbenzaldehyde via Darzen's reaction. 2) from para-Methylbenzy lchloride plus Hexamethyiene tetramine.

Taste threshold values

Taste characteristics at 10 ppm: sweet, fruity cherry with spicy an nutty nuances.

Synthesis Reference(s)

Synthetic Communications, 17, p. 677, 1987 DOI: 10.1080/00397918708075741