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Aromatization of 5-Hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione

SyntheticPage 840

DOI: 

Submitted: June 21, 2018, published: July 9, 2018

Authors

Andrew J. Smaligo (andrew.smaligo@gmail.com)

Brandon L. Frey (blfrey1@millersville.edu)

Steven Merwin Kennedy (Steven.Kennedy@millersville.edu)

A contribution from 

Reaction Scheme

Chemicals

5-Hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione (see ChemSpider Synthetic Page 800)

Triethylamine

Dichloromethane

Procedure

5-Hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione (0.12 g, 0.5 mmol) and Triethylamine (0.05 mL, 0.4 mmol) were dissolved in DCM (10 mL) at room temperature for one hour. The solvent was evaporated under reduced pressure to give aromatized product  (0.14 g, 87.0%) as a dark brown residue.

Author Comments

The product was not purified; compound 10 in Lead Reference (page 1322), 1,4-Dihydroxy-6-methyl-9,10-anthraquinone, produced via a similar procedure, was crystallized from petroleum ether.

Data

1H NMR (400 MHz, CDCl3): 2.55 (3H, s), 7.30 (1H, d), 7.62 (1H, d), 7.68 (1H, t), 7.83 (1H, d), 8.10 (1H, s), 8.2 (1H, d), 12.70 (1H, s).

13C NMR (100 MHz, CDCl3): 183.5, 182.8, 162.5, 146.1, 136.5, 135.8, 133.5 (2), 130.9, 127.8, 127.1, 124.4, 119.5, 116.5, 22.0.

M.p. 127 oC

Rf = 0.44 (1:9 EtOAc/Hex)

Lead Reference

Krohn, K., Tolkiehn, K., Lehne, V.; Schmalle, H. W.; Grutzmacher, H. Liebigs Ann. Chem. 1985, 7 ,1311–1328.

Supplementary Information

Keywords

aromatics/arenes, ketones, oxidation