The Reaction of Bicyclic Terpene Alcohols with Paraformaldehyde in the Presence of Acetic Anhydride and Sodium Acetate

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  • KISHIMOTO Takao
    Department of Applied Chemistry, Faculty of Science and Technology, Kinki University
  • MATSUBARA Yoshiharu
    Department of Applied Chemistry, Faculty of Science and Technology, Kinki University

Bibliographic Information

Other Title
  • 無水酢酸と酢酸ナトリウムの存在下における二環テルペンアルコールとパラホルムアルデヒドとの反応

Description

The reaction of bicyclic terpene alcohols, nopol(2-pinene-10-methanol) Cl J and isoborneol C 2, with paraformaldehyde (PFA) in the presence of acetic anhydride and sodium acetate was investigated, and three novel adducts were isolated by distillation and gas chromatography, respectively. Their structures were assigned on the basis of transesterification, their physical constants, IR, NMR and mass spectra as follows; nopyl acetoacetate C/ a, nopyl dioxymethyleneacetoacetate C/ b, nopyl trioxymethyleneacetoacetate 11 cD, isobornyl acetoacetate C2C a, isobornyl dioxymethyleneacetoacetate C2C b and isobornyltrioxymethyleneacetoacetate C2C c. The reaction of PFA with C 1 yields 11 a, C/ bp and CI c in a ratio of 71: 20: 9, and the reaction of PFA with C2C yields C2C a, C2C b and C2C c in a ratio of 80: 15: 5.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1974 (9), 1740-1743, 1974-09-10

    The Chemical Society of Japan

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