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
Chemicals Used
5-hydroxy-2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione (see page 800)
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.PNG13C-NMR_Diene.PNGFinal_Product.jpg
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Get structure file (.cdx, .sk2, .mol)
Keywords: alkenes, aromatics/arenes, oxidation
