4'-Hydroxypropiophenone

Chemical Properties

white powder

Uses

p-Hydroxypropiophenone is a 4-hydroxyphenyl ketone used in the preparation of potential antitumor agents. p-Hydroxypropiophenone is a lignin degrradation product.

Uses

Intermediates of Liquid Crystals

Uses

gonadotropic hormone inhibitor

Preparation

Preparation by Fries rearrangement of phenyl propionate
with aluminium chloride in refluxing carbon disulfide ? then at 130–150° for 2–3 h after solvent elimination (45–50%)
with aluminium chloride in nitrobenzene at 50° for 18 h (72%) or at ? 20° for 48 h (60%)
with aluminium chloride in nitromethane at 20° for 7–8 days (80%)
with aluminium chloride in chlorobenzene using microwave irradiation for ? 3 min at 106° (62%)
with aluminium chloride in ethylene dichloride at 95° for 5 h or in heptane at ? 80–90° for 7 h (36%), in benzene or in tetrachloroethane at 80°; with aluminium chloride in the presence of propionyl chloride at 50–60° for ? 6 h (49%)
with aluminium chloride without solvent at 50° for 10 h
with titanium tetrachloride in nitromethane at 20° for 7 days (56%) or ? without solvent at 50° for 10 h (39%)
with polyphosphoric acid at 100° (61%)
with boron trifluoride at 50° for 3 h (46%)
with stannic chloride at 50° for 3 h (10%).

Definition

ChEBI: P-Hydroxypropiophenone is a member of acetophenones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 2491, 1965 DOI: 10.1021/jo01018a528

Safety Profile

Poison by intraperitoneal, subcutaneous, and parenteral routes. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

target

Estrogen receptor

Purification Methods

4'-Hydroxypropiophenone [70-70-2] M 150.2, m 149o, b 140-145o/0.5mm, 8.05. Crystallise the phenone from H2O (m 149.8-150.2o) or EtOH (m 147o). The benzoyl derivative has m 117o, and the semicarbazone has m 183o (EtOH). [Beilstein 8 H 102, 8 II 104, 8 III 379.]