Synthesis of 2-methylanthraquinone

Preparation of 3-methylanthraquinone

Preparation of 3-methylanthraquinone

Preparation of 3-methylanthraquinone

20 grams of o-(p-toluyl)benzoic acid (2-(4-methylbenzoyl)benzoic acid) 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 3-methylanthraquinone 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-(p-toluyl)benzoic acid. The product, which need not be dried, is crystallized from ethanol yielding pure 2-methylanthraquinone, which melts at 173° C.

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

IUPAC Name

2-methylanthracene-9,10-dione

InChI

InChI=1S/C15H10O2/c1-9-6-7-12-13(8-9)15(17)11-5-3-2-4-10(11)14(12)16/h2-8H,1H3

InChI Key

NJWGQARXZDRHCD-UHFFFAOYSA-N

Canonical SMILES

CC1=CC2=C(C=C1)C(=O)C3=CC=CC=C3C2=O

MeSH Synonyms

2-methylanthraquinone

Depositor-Supplied Synonyms

2-Methylanthraquinone, 84-54-8, Tectoquinone, 2-methylanthracene-9,10-dione, Techtoquinone, Tectochinon, 9,10-Anthracenedione, 2-methyl-, 2-Methyl-9,10-anthraquinone, 2-Methylanthra-9,10-quinone, Anthraquinone, 2-methyl-, beta-Methylanthraquinone, 2-Methyl anthraquinone, NSC 607, .beta.-Methylanthraquinone, CHEMBL21745, CCRIS 5484, CHEBI:9427, NJWGQARXZDRHCD-UHFFFAOYSA-N, EINECS 201-539-6, SBB057251, AI3-15182, 2-Methyl-Anthraquinone, 9, 2-methyl-, ACMC-209pvh, AC1Q6JAO, UNII-Q9P233HWAJ, AC1L1N9V, DSSTox_CID_21439, DSSTox_RID_79734, Q9P233HWAJ, DSSTox_GSID_41439, SCHEMBL36822, KSC492Q0J, 65800_ALDRICH, NSC607, 2-methyl-9,10-anthracenedione, CTK3J2804, 2-methyl-anthracene-9,10-dione, NSC-607, MolPort-001-770-304, Anthraquinone, 2-methyl- (8CI), Tox21_302044, ANW-37803, AR-1E3832, QC-646, STL380671, ZINC03845299, AKOS000400281, AM62660, MCULE-5422309659, RP27383, RTR-031335, CAS-84-54-8, NCGC00255621-01, AJ-45836, AK114056, AN-24072, CJ-10804, L306, DB-056804, KB-173562, LS-171000, ST2417082, TR-031335, EU-0067001, FT-0613005, M0156, ST50826790, 2-methyl-9,10-dihydroanthracene-9,10-dione, C10405, AE-641/00352041, S14-0943, 3B3-036334, InChI=1/C15H10O2/c1-9-6-7-12-13(8-9)15(17)11-5-3-2-4-10(11)14(12)16/h2-8H,1H

Removed Synonyms

CID6773, C073955, 90389-55-2

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