4-Hydroxybenzophenone

Chemical properties

white to beige fine crystalline powder

The Uses of 4-Hydroxybenzophenone

4-Hydroxybenzophenone is used in the field of organic synthesis. It is used as pharmaceutical intermediate of clomifene citrate.

The Uses of 4-Hydroxybenzophenone

Metabolite of benzophenone.

Preparation

Preparation by condensation of benzotrichloride,
? with phenol in the presence of aluminium chloride in carbon disulfide at 0° (90%) or in the presence of zinc oxide in a water bath;
? with p-bromophenol in 30% sodium hydroxide solution at 80–85° (81%). There is substitution of the bromine atom by the benzoyl group.

Definition

ChEBI: 4-Hydroxybenzophenone is a member of benzophenones.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4674, 1955 DOI: 10.1021/ja01622a074
The Journal of Organic Chemistry, 19, p. 978, 1954 DOI: 10.1021/jo01371a016
Tetrahedron Letters, 31, p. 3943, 1990 DOI: 10.1016/S0040-4039(00)97513-0

Flammability and Explosibility

Not classified

Purification Methods

Dissolve p-benzoylphenol in hot EtOH (charcoal), filter and cool. Alternatively crystallise it once from EtOH/H2O and twice from *benzene [Grunwald J Am Chem Soc 73 4934 1951, Dryland & Sheppard J Chem Soc Perkin Trans 1 125 1986]. [Beilstein 8 IV 1263.]