Volume 24, Issue 4 pp. 965-969

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Benzofuran derivatives. Part 3^† On the reactivities of the intermediates in benzofuran synthesis

Takaaki Horaguchi,

Takaaki Horaguchi

Department of Chemistry, Faculty of Science, Niigata University, Ikarashi, Niigata 950-21, Japan

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Shinichi Matsuda,

Shinichi Matsuda

Department of Chemistry, Faculty of Science, Niigata University, Ikarashi, Niigata 950-21, Japan

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Kiyoshi Tanemura,

Kiyoshi Tanemura

Department of Chemistry, Faculty of Science, Niigata University, Ikarashi, Niigata 950-21, Japan

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Tsuneo Suzuki,

Tsuneo Suzuki

School of Dentistry at Niigata, The Nippon Dental University, Niigata, Hamaura-cho, Niigata 951, Japan

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Takaaki Horaguchi,

Takaaki Horaguchi

Department of Chemistry, Faculty of Science, Niigata University, Ikarashi, Niigata 950-21, Japan

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Shinichi Matsuda,

Shinichi Matsuda

Department of Chemistry, Faculty of Science, Niigata University, Ikarashi, Niigata 950-21, Japan

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Kiyoshi Tanemura,

Kiyoshi Tanemura

Department of Chemistry, Faculty of Science, Niigata University, Ikarashi, Niigata 950-21, Japan

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Tsuneo Suzuki,

Tsuneo Suzuki

School of Dentistry at Niigata, The Nippon Dental University, Niigata, Hamaura-cho, Niigata 951, Japan

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First published: July/August 1987

https://doi.org/10.1002/jhet.5570240414

Citations: 13

^†

Part 2, T. Suzuki, Bull. Chem. Soc. Japan, 58, 2821 (1985).

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Abstract

3-Methyl-5-nitrobenzofuran (2) and 3-methyl-5-nitrobenzofuran-2-carboxylic acid (3) were obtained by heating 2-acetyl-4-nitrophenoxyacetic acid (1) with various bases in acetic anhydride. It appeared that 3-hydroxy-3-methyl-5-nitro-2,3-dihydrobenzofuran-2-carboxylic acid (4) was the intermediate in the benzofuran synthesis. The properties of 4 were examined under various conditions. Using strong bases such as triethyl-amine in place of sodium acetate, 3-methyl-5-nitrobenzofuran-2-carboxylic acid (3) was obtained exclusively. However, in the presence of acetic acid in the reaction mixture 3-methyl-5-nitrobenzofuran (2) was obtained in good yield. The reaction pathways for the formation of 2 and 3 are discussed.

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Volume24, Issue4

July/August 1987

Pages 965-969

Benzofuran derivatives. Part 3^† On the reactivities of the intermediates in benzofuran synthesis

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Benzofuran derivatives. Part 3† On the reactivities of the intermediates in benzofuran synthesis

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Benzofuran derivatives. Part 3^† On the reactivities of the intermediates in benzofuran synthesis