Oxidation of 2-methoxy-6-(1-methylethyl)naphthalene with oxygen |
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Authors: | Beata Orlińska Zbigniew Stec and Jan Zawadiak |
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Institution: | (1) Department of Organic Chemical Technology and Petrochemistry, Silesian University of Technology, Gliwice, Poland |
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Abstract: | 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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