Epoxidation of 1,4-naphthoquinone; 2,3-Epoxy-1,4-naphthoquinone
SyntheticPage 839
DOI:
10.1039/SP839
Submitted Jun 16, 2018, published Jun 17, 2018
Robert Smith (
rbsmith@uclan.ac.uk), James Davis (
James.Davis@ulster.ac.uk), Maria Marti Villalba (
), Lucy Lee (
)
A contribution from
Smith Group
Chemicals Used
1,4-Naphthoquinone (Sigma Aldrich)
Hydrogen Peroxide 30% (Sigma Aldrich)
Procedure
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.
Data
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. https://doi.org/10.1016/j.elecom.2009.05.056
Other References
Supplementary Information
1,4-Naphthoquinone epoxide 13C.pdf1,4-Naphthoquinone Epoxide.pdf
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Keywords: epoxidation, ketones