Synthesis of β-Nitro Ketones from α, β-Unsaturated Ketones with Sodium Nitrite-Acetic Acid

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  • MIYAKOSHI Tetsuo
    Department of Industrial Chemistry, Faculty of Engineering, Meiji University
  • SAITO Shojiro
    Department of Industrial Chemistry, Faculty of Engineering, Meiji University

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Other Title
  • α,β-不飽和ケトン類を用いるβ-ニトロケトン類の合成
  • α，β‐不飽和ケトン類を用いるβ‐ニトロケトン類の合成

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Description

Synthesis of β-nitro ketones [2] from α, β-unsaturated ketones [1] was studied. In the reaction of 3-buten-2-one [1a] with sodium nitrite-acetic acid in THF, 4-nitro-2-butanone [2a] was obtained in 82% yield. When THF is displaced with DMSO in the above reaction, trans-3-octene-2, 7-dione [3] was formed in 56% yield together with 30% yield of 4-nitro-3butanone [2a]. Furthermore, the use of potassium nitrite instead of sodium nitrite in THF yielded 35% of the dimer [3] and 18% of 4-nitro-2-butanone [2a]. The reaction of α, βunsatur ated ketones [1] which did not bear substituents in the olefinic part with sodium nitrite-acetic acid in THF gave the corresponding, β-nitro ketones [2] in 42-82% yield.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1984 (3), 458-462, 1984-03-10

    The Chemical Society of Japan

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