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Alkaline Air Oxidation of 5-hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione; Dihydroanthraquinone

SyntheticPage 801
DOI: 10.1039/SP801
Submitted Oct 13, 2015, published Oct 28, 2015
Jevica Salim (jev340@gmail.com), Steven M. Kennedy (steven.kennedy@millersville.edu)
A contribution from Kennedy Group, Millersville University


			Reaction Scheme: <IMG src="/images/empty.gif">Alkaline Air Oxidation of <SPAN id=csm1471530235698 class="csm-chemical-name csm-not-validated" title=5-hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione grpid="2">5-hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione</SPAN><IMG alt="" src="/images/empty.gif"><IMG src="/images/empty.gif">

Chemicals Used

5-hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione (see page 800)

Sodium Hydroxide, 2 M 

Hydrochloric Acid, 37%

Procedure

5-hydroxy-2-methyl-4,4a,9,9a-tetrahydroanthracene-9,10-dione (1.7428 g, 7.25 mmol) was dissolved in 2 M sodium hydroxide (20 mL) and stirred vigorously open to air for approximately twenty minutes. The resulting thick, dark-brown mixture was cooled to 0 °C and acidified with hydrochloric acid dropwise. The mixture was filtered, washed with water, and dried. The crude product was recrystallized from ethanol to yield 5-hydroxy-2-methyl-1,4-dihydroanthracene-9,10-dione as golden-brown needles (0.9980 g, 57% yield).

Author's Comments

The reaction mixture turns a shade of green when it has been acidified. 

Data

1H NMR (400 MHz, CDCl3): 1.81 (s, 3H), 3.12 (m, 2H), 3.23 (m, 2H), 5.55 (m, 1H), 7.22 (m, 1H), 7.56-7.63 (m, 2 H), 12.11 (s, 1H). 

 

13C NMR (100 MHz, CDCl3): 22.92, 25.08, 29.18, 130.10, 132.06, 141.69, 142.90, 183.87, 189.81.

 

Melting Point: 146.2-148.8 °C


Lead Reference

Burns, C. J.; Gill, M.; Saubern, S. Aust. J. Chem. 1991, 44, 1427-1445.

Supplementary Information

1H-NMR_Diene.PNG
13C-NMR_Diene.PNG
Final_Product.jpg

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

Keywords: alkenes, aromatics/arenes, oxidation

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