Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Hydration of Myrcene or Isoprene with Halogenated Acetic Acid
Studies on the Hydration of Terpenes.IV
Yoshiharu MATSUBARAKiyofumi TANAKAHiroshi IMASHIRO
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JOURNAL FREE ACCESS

1974 Volume 32 Issue 7 Pages 524-527

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Abstract
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.
(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.
Conversion is 81% under the best conditions. The content of (5) plus (9) in the hydration products is 51% under the best conditions.
(2) yielded the following three alcohols : (7), (8), (9); two unidentified compounds were also found in small amounts.
(8) is the main product (68%) from the monoterpene alcohols when the hydration is carried out in the presence of a solvent.
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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© The Society of Syhthetic Organic Chemistry, Japan
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