Hydration of Myrcene or Isoprene with Halogenated Acetic Acid

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  • MATSUBARA Yoshiharu
    Department of Applied chemistry, Faculty of Science and Technology, Kinki University
  • TANAKA Kiyofumi
    Department of Applied chemistry, Faculty of Science and Technology, Kinki University
  • IMASHIRO Hiroshi
    Department of Applied chemistry, Faculty of Science and Technology, Kinki University

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Other Title
  • ミルセンあるいはイソプレンの置換ハロゲン酢酸を用いる水和反応
  • ミルセン アルイハ イソプレン ノ チカン ハロゲン サクサン オ モチイル スイワ ハンノウ
  • Studies on the Hydration of Terpenes.IV
  • テルペン類の水和反応に関する研究 (第4報)

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Hydration was studied for myrcene (1) or isoprene (2) with halogenated acetic acid under following conditions ; the equimolar mixtures of (1) or (2) and halogenated acetic acid (monochloro-, dichloro- or trichloroacetic acid) was stirred in flask with or without dichloroethane, benzene, n-hexane or water.<BR>(1) yielded the following six alcohols : linallol (3), myrcenol (5), 3, 7-dimethyl-1, 3-octadiene-7-ol (6), β-terpineol (7), α-terpineol (8), geraniol (9); two unidentified compounds were also found in small amounts.<BR>Conversion is 81% under the best conditions. The content of (5) plus (9) in the hydration products is 51% under the best conditions.<BR>(2) yielded the following three alcohols : (7), (8), (9); two unidentified compounds were also found in small amounts.<BR>(8) is the main product (68%) from the monoterpene alcohols when the hydration is carried out in the presence of a solvent.<BR>When dichloroacetic acid was used as a telogen in the absence of a solvent, the content of (9) in the monoterpene alcohols was 53%.

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