On the Formation of Borncol from Turpentine Oil (III) : Action of Picric Acid and Styphnic Acid on Turpentine Oil.

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  • テレビン油よりボルネオールの生成(第三報) : テレビン油に對するピクリン酸の作用 : (附テレビン油とスチフニン酸との作用)

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Description

Lextreit (C. r. 102, 555 ; Ber. 19, Ref. 237) heated French turpentine oil with picric acid at 150° and obtained a picrate C10H16·C6H2 (NO2)3OH (m.p. 133°), which when heated with aqueous alkali gave laevorotatory borneol. Some years later a similar research was made by Tilden and Forster (Soc.63, 1388) who boiled the some picrate with aqueous potash or baryta and obtained optically inactive bomeol. They also identified dipentene (dihydrochloride m. p. 50°) in the reaction liquor, but not camphene. The experiments of the present authors on the same subject differs in several respects from those previously obtained. The pinene fraction was prepared from both laevo and dextro rotatory American turpentine oil by distillation over sodium, the boiling point and optical rotation being 158-161° and -8.00°, +8.55° respectively. On heating with picric acid on water bath the laevo rotatory oil yielded l-picrate (m. p. 133°), from which l-bomeol (43% of the picrate) was obtained, while the dextro rotatory oil by the same treatment gave i-picrate, from which i-borneol was obtained. In addition to the picrates above mentioned the authors succeded in isolating a new isomeric picrate. The mother liquor of the picrate above described was shaken with water and then distilled with steam. The thick residue was mixed with alcohol and allowed to stand over night, when crystals separated out, which were washed with large quauatity of water and then recrystallised from boiling alcohol. It formed yellowish plate melting at 97-99°.Analysis 0.2500g gave 25.6cc N at 21, ° 758mm. N% found 11.57 calc for C10H16-C6H2(NO2)3OH 11.50 Styphnic acid (trinitroresorcinol) reacts with turpentine oil in the same manner as picric acid, but the yield of borneol was very small.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 1924 (513), 909-913, 1924

    The Pharmaceutical Society of Japan

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