Print version Print setup

Oxidation of 1,4,4a,9a-tetrahydro-2,3-dimethyl-9,10-anthracenedione
; 2,3-dimethyl-9,10- Anthracenedione

SyntheticPage 937
Submitted Sep 25, 2020, published Nov 09, 2020
Steven Kennedy (Steven.Kennedy@millersville.edu), Autumn Peters (anpeters@millersville.edu)
A contribution from Kennedy Group, Millersville University


			Reaction Scheme: <div><strong></strong></div>
<div><strong></strong></div>
<div><strong></strong></div>
<div>Oxidation of 1,4,4a,9a-tetrahydro-2,3-dimethyl-9,10-anthracenedione<strong> </strong><!--  /* Font Definitions */  @font-face 	{font-family:"Cambria Math"; 	panose-1:2 4 5 3 5 4 6 3 2 4; 	mso-font-charset:0; 	mso-generic-font-family:roman; 	mso-font-pitch:variable; 	mso-font-signature:3 0 0 0 1 0;}  /* Style Definitions */  p.MsoNormal, li.MsoNormal, div.MsoNormal 	{mso-style-unhide:no; 	mso-style-qformat:yes; 	mso-style-parent:""; 	margin:0in; 	mso-pagination:widow-orphan; 	font-size:12.0pt; 	font-family:"Times New Roman",serif; 	mso-fareast-font-family:"Times New Roman";} .MsoChpDefault 	{mso-style-type:export-only; 	mso-default-props:yes; 	font-size:11.0pt; 	mso-ansi-font-size:11.0pt; 	mso-bidi-font-size:11.0pt; 	font-family:"Calibri",sans-serif; 	mso-ascii-font-family:Calibri; 	mso-ascii-theme-font:minor-latin; 	mso-fareast-font-family:Calibri; 	mso-fareast-theme-font:minor-latin; 	mso-hansi-font-family:Calibri; 	mso-hansi-theme-font:minor-latin; 	mso-bidi-font-family:"Times New Roman"; 	mso-bidi-theme-font:minor-bidi;} .MsoPapDefault 	{mso-style-type:export-only; 	margin-bottom:8.0pt; 	line-height:107%;}size:8.5in 11.0in; 	margin:1.0in 1.0in 1.0in 1.0in; 	mso-header-margin:.5in; 	mso-footer-margin:.5in; 	mso-paper-source:0;} div.WordSection1 	{page:WordSection1;}--></div>

Chemicals Used

1,4,4a,9a-tetrahydro-2,3-dimethyl-9,10-anthracenedione [936]

Potassium Hydroxide (Carolina Biological Supply Company)

Ethanol (200 proof, Pharmco)

Diethyl Ether (BHT stabilized, Fisher Scientific)

Procedure

In a round-bottom flask with a reflux condenser, 1,4,4a,9a-tetrahydro-2,3-dimethyl-9,10-anthracenedione (0.24 g, 1 mmol) was dissolved in 3.6 mL of a 5% w/w ethanolic KOH solution. The solution was stirred and heated at 45 °C, overnight. After approx. 12 hours, the flask was removed from heat and allowed to cool to room temperature. The solid product was filtered using vacuum filtration and washed with water, ethanol, and diethyl ether. The product (2,3- dimethyl-9,10-anthracenedione) was allowed to air dry overnight yielding a light-green powder (0.21 g, 89%).

Author's Comments

The reaction solution changes coloration from green initially to a distinct yellow following reaction completion.

This reaction has been performed from a 1 to 40 mmol scale where each reaction resulted in good yield and purity.

Residual water and ethanol peaks can be seen on the 1H NMR which can be resolved by further drying methods.

Data

1H NMR (400 MHz, CDCl3): δ 8.22 (t, 2H, J = 4.8 Hz), 8.10 (s, 2H), 7.78 (t, 2H, J = 4.4 Hz), 2.45 (s, 6H)

13C NMR (100 MHz, CDCl3): δ 183.34, 144.06, 142.37, 133.83, 133.66, 128.16, 127.06, 20.24

Rf = 0.39 (1:9 EtOAC/Hex)

M.p. 214.6 - 215.5°C


Lead Reference

Allen, C. F. H.; Bell, A. Organic Syntheses. 1942, 22, 37-8.

Supplementary Information

IR_2,3-diMe-9,10-Anthracenedio (2,3-dimethyl-9,10-Anthracenedione_IR.pdf)
2,3-dimethyl-9,10-Anthracenedi (2, 3- dimethyl-9, 10- Anthracenedione_1HNMR.png)
13CNMR_2,3-dimethyl-9,10-Anthr (2, 3- dimethyl-9, 10- Anthracenedione_CNMR.png)

This page has been viewed approximately 324 times since records began.

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

Keywords: alkenes, aromatics/arenes, ketones, oxidation

Post new comment
Loading ...