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Epoxidation of 1,4-naphthoquinone; 2,3-Epoxy-1,4-naphthoquinone

SyntheticPage 839
Submitted Jun 16, 2018, published Jun 17, 2018
Robert Smith (, James Davis (, Maria Marti Villalba (), Lucy Lee ()
A contribution from Smith Group

			Reaction Scheme: <IMG src="/images/empty.gif">Epoxidation of <SPAN id=csm1531323546856 class=csm-chemical-name title=1,4-naphthoquinone grpid="1">1,4-naphthoquinone</SPAN><IMG src="/images/empty.gif">

Chemicals Used

1,4-Naphthoquinone (Sigma Aldrich)

Hydrogen Peroxide 30% (Sigma Aldrich)


Into a boiling tube (A) was placed either 1,4-naphthoquinone (0.91 g, 5.8 mmol) and ethanol (10 mL) and the tube was heated in a water bath until the entire solid dissolved. Into a second boiling tube (B) was added sodium carbonate (0.2 g), distilled water (5 mL) and cold 30% hydrogen peroxide (2 mL). Boiling tube A was placed under a cold tap until very slight crystallization occurred, then boiling tube B was added to A in one go. With swirling, boiling tube A was cooled in ice water which produced a white solid. The solid was isolated at the pump and washed with water (3 × 10 ml).  The solid was dried at the pump to yield 2,3-epoxy-1,4-naphthoquinone (0.39 g, 39%) as white crystals.

Author's Comments

Should a yellow colour still be present upon addition of the hydrogen peroxide, stir the reaction mixture until the colour subsides.  Its recommended that 1,4-naphthoquinone is purified by column chromatography before use on a silica column using chloroform as eluent.


 1H NMR δ: 7.97–7.94 (m, 2H, Ar-H) 7.75–7.73 (m, 2H, Ar-H); 4.00 (s, 2H, C–H),  13C NMR δ: 55.24, 127.16, 131.69, 134.67, 190.68. LCMS – ESI (mz) 174 [M-H].

Lead Reference

Lucy Lee, Maria Marti Villalba, Robert B.Smith and JamesDavis Epoxide–quinone transformations: Multi-parametric indicators for assessing animal welfare, Electrochemistry Communications 11 (2009) 1555–1558.

Other References

Supplementary Information

1,4-Naphthoquinone epoxide 13C.pdf
1,4-Naphthoquinone Epoxide.pdf

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

Keywords: epoxidation, ketones

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