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Oxidation of 2-methoxy-6-(1-methylethyl)naphthalene with oxygen

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Abstract

Aerobic oxidation of 2-methoxy-6-(1-methylethyl)naphthalene to hydroperoxide, alcohol, and ketone, is reported. These compounds, particularly 2-acetyl-6-methoxynaphthalene, are important intermediates in naproxen synthesis. N-Hydroxyphthalimide is shown here to be an efficient catalyst for oxidation to the hydroperoxide, 2-methoxy-6-(1-hydroperoxy-1-methylethyl)naphthalene, with a yield of 87%. However, the ketone and alcohol were obtained with lower yields, with a maximum yield of 13% for the ketone and 27% for the alcohol, using N-hydroxyphthalimide and Cu(II) acetylacetonate as a catalyst. The synthesis of the products 2-acetyl-6-methoxynaphthalene and 2-methoxy-6-(1-hydroxy-1-methylethyl)naphthalene via an initial oxidation step to the hydroperoxide followed by a hydroperoxide decomposition step is shown to be more efficient; the ketone and alcohol were obtained from 2-methoxy-6-(1-methylethyl)naphthalene with yields of 40 and 56%, respectively.

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Acknowledgments

We are grateful to the Ministry of Science and Higher Education of Poland for financial support (grant no. N N209 153836).

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Authors and Affiliations

  1. Department of Organic Chemical Technology and Petrochemistry, Silesian University of Technology, Gliwice, Poland

    Beata Orlińska, Zbigniew Stec & Jan Zawadiak

Authors
  1. Beata Orlińska
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  2. Zbigniew Stec
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  3. Jan Zawadiak
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Correspondence to Beata Orlińska.

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Orlińska, B., Stec, Z. & Zawadiak, J. Oxidation of 2-methoxy-6-(1-methylethyl)naphthalene with oxygen. Monatsh Chem 143, 295–301 (2012). https://doi.org/10.1007/s00706-011-0630-3

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  • DOI: https://doi.org/10.1007/s00706-011-0630-3

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