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Reduction of 1,8-Dihydroxyanthraquinone; 1,8-Dihydroxyanthrone

SyntheticPage 875
Submitted Jan 07, 2019, published Jan 09, 2019
Robert Smith (rbsmith@uclan.ac.uk), Megan Critchley (MCritchley@uclan.ac.uk), Clare Lawrence (CLLawrence@uclan.ac.uk)
A contribution from Smith Group


			Reaction Scheme: Reduction of 1,8-Dihydroxyanthraquinone

Chemicals Used

1,4-Dihydroxyanthraquinone (Sigma Aldrich).

Glacial acetic acid (Fisher Scientific).

Anhydrous tin (II) chloride (Sigma Aldrich).

Concentrated hydrochloric acid (Fisher Scientific).

Procedure

To a round-bottomed flask* charged with 1,8-dihydroxyanthraquinone (0.24 g, 1 mmol) and glacial acetic acid (20 mL) was slowly added a warm** solution of anhydrous tin (II) chloride (2.14, 11.29 mmol) in conc. hydrochloric acid (11 mL).  The reaction mixture was heated at reflux for 24 hours with constant stirring.  The reaction mixture was allowed to cool and slowly poured over ice water to yield a yellow solid.  The solid was isolated by vacuum filtration on a Buchner funnel to yield 1,8-dihydroxyanthrone (0.20g, 88%) as a yellow solid.

Author's Comments

*A round-bottomed flask fitted with a reflux condenser was used which fitted snugly into a metal heating block.  A thermocouple was used to control the temperature and the reaction was open to the air (no inert gasses were required).  Stirring was accomplished using a stirring bar, which was controlled from the hot plate.  The whole reaction was accomplished in the open air without the need of dry/inert conditions.

** The solution was at 40°C.

Data

1H NMR (300 MHz, DMSO-d6) δ 12.09 (s, 2H), 7.61 (t, J = 7.9 Hz, 2H), 7.03 (dd, J = 7.6, 1.3 Hz, 2H), 6.90 (d, J = 8.3 Hz, 2H), 4.47 (s, 2H).  13C NMR (75 MHz, DMSO) δ 194.05, 162.29, 143.31, 137.17, 119.65, 115.77, 115.32, 32.73. GC-MS EI [M]: 226.73


Lead Reference

Jiro Motoyoshiya, Yusuke Masue, Yoshinori Nishi and Hiromu Aoyama, Synthesis of Hypericin via Emodin Anthrone Derived from aTwo-fold Diels-Alder Reaction of 1,4-Benzoquinone, Natural Product Communications, 2007, 2(1), 67 – 70.

Supplementary Information

e.g. Actual NMR spectra (as images or jdx files for interactive spectra), photographs of apparatus, TLC’s or crystals or videos. Please contact the ChemSpider team (ChemSpider-at-rsc.org) for help with this.
1H NMR (1H.pdf)
13C NMR (13C.pdf)
135-DEPT NMR (135-DEPT.pdf)
135-DEPT vs 13C (135-DEPT vs 13C.pdf)
1H 1H COSY (1H1H COSY.pdf)
MS (MS.pdf)

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Keywords: aromatics/arenes, heterocyclic compounds, ketones, reduction

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