2,4-Dihydroxyacetophenone

Chemical properties

2,4-Dihydroxyacetophenone appears as a yellow-brown to reddish-brown fine crystalline powder. It slowly decomposes in water and can dissolve in hot alcohol, pyridine, and glacial acetic acid. In contrast, it is nearly insoluble in ether, benzene, and chloroform. A reaction with iron chloride causes it to adopt a red hue.

The Uses of 2,4-Dihydroxyacetophenone

2,4-Dihydroxyacetophenone is used as intermediate for pharmaceuticals.

The Uses of 2,4-Dihydroxyacetophenone

2,4-Dihydroxyacetophenone (cas# 89-84-9) is a compound useful in organic synthesis. It is also used as intermediate for pharmaceuticals. Reagent for iron as a 10% alcoholic solution. A red color is obtained with ferric ions in slightly acid solution: Cooper, Ind. Eng. Chem. Anal. Ed. 9, 334 (1937).

Definition

ChEBI: 2',4'-dihydroxyacetophenone is a dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'. It has a role as a plant metabolite. It is a member of resorcinols and a dihydroxyacetophenone.

Preparation

Preparation by reaction of acetic acid on resorcinol,
with zinc chloride (Nencki reaction) (94%)
with boron trifluoride
with Amberlite IR-120 (a cation exchange resin, sulfonic acid type) (87%)
with polyphosphoric acid (63%)
with 70% perchloric acid (33%).

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 428, 1948 DOI: 10.1021/ja01181a521

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. A severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

2,4-Dihydroxyacetophenone is obtained by the acetylation of resorcinol and acetic acid. In addition, it can also be obtained by reacting resorcinol with chloroacetyl or acetic anhydride in the presence of zinc chloride.