Synthesis of anthracen-9-ol

Preparation of anthracen-9-ol

Preparation of anthracen-9-ol

Preparation of anthracen-9-ol

10 g of anthraquinone and 30 g of granulated zinc are refluxed with 500 ml of glacial acetic acid, the operation being performed in a good fume cupboard. Conc. hydrochloric acid, a few ml at a time, is added until no coloration occurs, and hydrogen is continuously evolved. After  hour and when a sample no longer deposits crystals on cooling, the whole is cooled, poured into dilute hydrochloric acid, and the precipitate recrystallised from glacial acetic acid, to which a little zinc dust and hydrochloric acid have been added to prevent reoxidation. The yield of  anthracen-9-ol 80%, colourless needles; insoluble in water; m.p. 170° C (dec.).

Systematic organic chemistry, by W. M. Cumming, 187-188, 1937.

IUPAC Name

anthracen-9-ol

InChI

InChI=1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9,15H

InChI Key

AUKRYONWZHRJRE-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C=C3C=CC=CC3=C2O

MeSH Synonyms

1,8 Dihydroxy 9 anthrone, 1,8,9-Anthracenetriol, 1,8-Dihydroxy-9(10H)-anthracenone, 1,8-Dihydroxy-9-anthrone, Anthraforte, Anthralin, Anthranol, Bioglan Brand of Anthralin, Cahill May Roberts Brand of Anthralin, Cignolin, Cygnoline, Dermal Brand of Anthralin, Dihydroxyanthranol, Dithranol, Dithrocream, Ditranol FNA, FNA Brand of Anthralin, Hamilton Brand of Anthralin, Lasan, Micanol, Psoradrate, Psoricrème, Schering Plough Brand of Anthralin, Schering-Plough Brand of Anthralin, Stiefel Brand 1 of Anthralin, Stiefel Brand 2 of Anthralin, Vinas Brand of Anthralin

Depositor-Supplied Synonyms

anthracen-9-ol, 9-Anthracenol, Anthranol, 529-86-2, 9-Hydroxyanthracene, 9-Anthranol, 9-Anthrol, Anthracene, 9-hydroxy-, ANF, 2bjm, 9-Anthrol (8CI), 9-Anthracenol (9CI), AC1L1VTQ, UNII-15PF96Z0OC, SCHEMBL437148, 15PF96Z0OC, CHEBI:40753, CTK1H1705, AUKRYONWZHRJRE-UHFFFAOYSA-N, MolPort-020-014-315, NSC39886, ZINC1671624, NSC 39886, NSC-39886, ZINC01671624, AKOS015856314, AJ-29220, AK151481, PL003256, PL058659, SC-67278, DB-022052, TR-018759

Removed Synonyms

ANTHRONE, CID10731

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