1,3-Diphenylacetone

Chemical properties

1,3-Diphenyl-2-propanone has a sweet, faint, fruity odor reminiscent of bitter almond

Physical properties

White crystals or colorless crystalline mass. M.P. 40°C. B.P. 331°C.
1,3-Diphenylacetone is almost insoluble in water, soluble in alcohol and oils, poorly in Propylent glycol. Sweet, but rathtr faint, fruity-almondy odor of considerable tenacity.

The Uses of 1,3-Diphenylacetone

1,3-Diphenylacetone is used in the aldol condensation reaction with benzil (a dicarbonyl) and base to create tetraphenylcyclopentadienone.

Preparation

By heating α,?α’-phenyl benzyl ethylene glycol or α,?α’-phenyl benzyl ethylene oxide in the presence of diluted H2SO4 or ZnCl2; also by dry distillation of phenylacetate and magnesium chloride (C6H5CH2COOMgCl) or other salts of phenylacetic acid.

Definition

ChEBI: 1,3-Diphenyl-2-propanone is an aromatic compound.

What are the applications of Application

1,3-Diphenylacetone is occasionally used as a trace ingredient in floral perfums compositions, Fougere types, New Mown Hay, etc. wh:re it can act as a modifier for Coumarin, making its odor softer.
Used in fruit flavor compositions, and in imitation Honey, Nut, etc. - mostly in tracss only.

Aroma threshold values

Aroma characteristics at 10% in ethanol. Sweet, powdery, and honey with floral rose nuances

Taste threshold values

Taste characteristics at 30 ppm: bitter with floral, rose and honey notes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 869, 1968 DOI: 10.1021/jo01266a094

Purification Methods

Fractionally crystallise it from its melt, then crystallise it from pet ether. Store it in the dark. [Beilstein 7 IV 1420.]