Hydrochloric Acid → Perilla alcohol

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In 1980 Lazare and co-workers reported a ninety percent (90%) yield of a diol that was obtained by treating beta-pinene oxide with mercury (II) salts in tetrahydrofuran/water solutions. (J. Chem. Soc. Perkin Trans I 1980, 1747). The diol was extracted with chloroform followed by its reaction with 1.5 N. hydrochloric acid to give an eighty-five percent (85%) yield of perillyl alcohol based on the initial beta pinene oxide. The applicants could not reproduce the acid-catalyzed dehydration using 1.5 N HCl despite trying numerous variations of the experimental conditions reported. The applicants found this process to produce perillyl alcohol in a yield of less than ten percent. In every case complex mixtures of products were obtained. It was stated that both p-menth-1-ene-7, 8 diol and 7-acetoxy-p-menth-1-en-8-ol are fragrance compounds but no experimental procedures describing their preparation were presented.

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