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Aromatization of 5-Hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione; 1-hydroxy-6-methylanthracene-9,10-dione

SyntheticPage 840
DOI: 10.1039/SP840
Submitted Jun 21, 2018, published Jul 09, 2018
Steven Merwin Kennedy (Steven.Kennedy@millersville.edu), Andrew J. Smaligo (andrew.smaligo@gmail.com), Brandon L. Frey (blfrey1@millersville.edu)
A contribution from Kennedy Group, Millersville University


			Reaction Scheme: <img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />Aromatization of <span id="csm1531319106928" class="csm-chemical-name csm-not-validated" title="5-Hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione">5-Hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione</span><img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />

Chemicals Used

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's 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

CNMR.pdf
1H-NMR (HNMR.pdf)
Zoom-1H-NMR (ZoomHNMR.pdf)

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Get structure file (.cdx, .sk2, .mol)

Keywords: aromatics/arenes, ketones, oxidation

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