686. Anthranol

Nomenclature

CAS number: 529-86-2
9-Anthracenol; 9-anthrol; 9-hydroxyanthracene.
C14H10O; mol wt 194.23.
C 86.57%, H 5.19%, O 8.24%.

Description and references

Prepd by dissolving anthrone in 5 to 10% boiling NaOH soln, cooling to 5° and pouring in cooled 5% H2SO4: Meyer, Ann. 379, 56 (1911). Also prepared from anthraquinone.

Chemical structure

Properties

Needles from glacial acetic acid, plates from dil alcohol. Orthorhombic, mp 120° (if bath is heated to 110°). Sinters at 120°, mp 152° (if bath is cold at start). Absorption spectrum (of acetate): Barnett et al., J. Chem. Soc. 1928, 885. Sol in most solvents with blue fluorescence. The solid is fairly stable when kept dry. In solution it changes quickly to anthrone. Recrystallizations of anthranol may lead to a less pure compound.

Derivative

Acetate.
C16H12O2; mol wt 236.27.
C 81.34%, H 5.12%, O 13.54%.

Properties

Crystals from petr ether, mp 134°.

Derivative

Benzoate.
C21H14O2; mol wt 298.33.
C 84.55%, H 4.73%, O 10.73%.

Properties

Crystals from pyridine + alcohol, mp 170-172°.

Derivative

Methyl ether.
C15H12O; mol wt 208.26.
C 86.51%, H 5.81%, O 7.68%.

Properties

Crystals from alcohol, mp 97-98°.

Derivative

Ethyl ether.
C16H14O; mol wt 222.28.
C 86.45%, H 6.35%, O 7.20%.

Properties

Crystals from methanol, mp 73°.

Use

In the manuf of dyes.