Synthesis of anthraquinone (anthracenedione; dioxoanthracene)

Preparation of anthraquinone

Preparation of anthraquinone (anthracenedione; dioxoanthracene)

Preparation of anthraquinone (anthracenedione; dioxoanthracene)

20 grams of o-benzoylbenzoic acid (either hydrated or anhydrous) is heated with 100 ml of concentrated sulfuric acid for 1 hour. The mixture should be shaken at the start so that all of the solid dissolves rapidly. The color changes from red to brown. The anthraquinone formed is precipitated by pouring the hot solution onto about 1 kg of ice. Digestion of the precipitate, accomplished by heating the mixture for a short time at the boiling point, gives a more granular product. This is collected by filtration, washed well with water and then with a little dilute ammonia in order to remove traces of unchanged o-benzoylbenzoic acid. The product, which need not be dried, is crystallized from glacial acetic acid yielding pure anthraquinone, which melts at 286° C.

Experiments in Organic Chemistry, L. F. Fieser, 190, 1941

IUPAC Name

anthracene-9,10-dione

InChI

InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H

InChI Key

RZVHIXYEVGDQDX-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3C2=O

MeSH Synonyms

9,10-anthracenedione, 9,10-anthraquinone, 9,10-anthraquinone, radical ion (1-)

Depositor-Supplied Synonyms

ANTHRAQUINONE, 9,10-Anthraquinone, 9,10-Anthracenedione, anthracene-9,10-dione, 84-65-1, Anthradione, Hoelite, Corbit, Morkit, 9,10-Dioxoanthracene, Anthra-9,10-quinone, 9,10-Anthrachinon, Anthrapel, 9,10-quinone, Az-Q, CHEBI:40448, Caswell No. 052A, NSC 7957, Anthracene-9,10-quinone, Anthraquinone [BSI:ISO], Bis-alkylamino anthraquinone, 9,10-Anthrachinon [Czech], CCRIS 649, Anthracene, 9,10-dihydro-9,10-dioxo-, CHEMBL55659, HSDB 2074, RZVHIXYEVGDQDX-UHFFFAOYSA-N, EINECS 201-549-0, 9,10-dihydro-9,10-dioxoanthracene, SBB060613, EPA Pesticide Chemical Code 122701, NCGC00094960-03, DSSTox_CID_95, AI3-09073, DSSTox_RID_75364, DSSTox_GSID_20095, CAS-84-65-1, Anthrachinon, Morkie, Anthracenequinone, 9,10-anthrachinoe, 9,10-Anthracendion, Spectrum_001527, SpecPlus_000645, AC1L1NAG, Spectrum2_000405, Spectrum3_001501, Spectrum4_000907, Spectrum5_001897, PS926_SUPELCO, ACMC-209pw0, Anthra-9,10-quinone #, Epitope ID:116191, UNII-030MS0JBDO, AC1Q6JY1, 030MS0JBDO, SCHEMBL14943, A90004_ALDRICH, BSPBio_003141, KBioGR_001374, KBioSS_002007, KSC362C5J, DivK1c_006741, SPECTRUM1502103, SPBio_000330, 45327_RIEDEL, KBio1_001685, KBio2_002007, KBio2_004575, KBio2_007143, KBio3_002641, NSC7957, MolPort-001-783-170, HMS1921J14, NSC-7957, Tox21_111369, 9,10-dihydroanthracene-9,10-dione, ANW-37822, AR-1H7445, BBL003001, CCG-39966, DNC009075, STK398385, ZINC03847491, Anthracene,10-dihydro-9,10-dioxo-, AKOS000282964, Tox21_111369_1, LS-1837, MCULE-4655011423, RP26414, RTR-031315, TRA0074021, NCGC00094960-01, NCGC00094960-02, NCGC00094960-04, NCGC00094960-06, AC-12719, AJ-45864, AK117080, AN-24075, K513, KB-74706, DB-005409, TR-031315, A0502, FT-0622417, ST24024605, ST50410412, T8216, C16207, AB-131/40003277, 3B4-0198, I14-1219, Melting point standard 283-286 inverted exclamation markaC, 90530-46-4, InChI=1/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8

Removed Synonyms

Anthracenedione, CID6780, c1011, 9,10-anthraquinone, radical ion (1-), A-8000, C042834, 790240-52-7, 9TA

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *