Abstract
AbstractThe mixture obtained from the well‐known BF3‐catalyzed condensation of camphene and phenol contains at least nine terpeno‐phenols. The major components are o‐ (p‐) (2,2, exo‐3‐trimethyl‐exo‐5‐norbornyl)‐phenols, accompanied by some o‐ (p‐) (exo‐2‐borny1)‐phenols and smaller amounts of o‐ (p‐) (1,3,3‐trimethyl‐exo‐6‐norborny1)‐ phenols. Further, very small amounts (>1%) of the three corresponding meta‐substituted phenols also occur in the condensation mixture. On catalytic hydrogenation, these m‐isomers lead to 3‐terpenyl‐cyclohexanols characterized by a powerful odour of sandalwood. Most surprisingly, the 2‐ and 4‐terpenyl‐cyclo‐hexanols obtained in the same way from the o‐ and p‐terpenyl‐phenols are almost odourless. The sandalwood odour appears, therefore, to be highly characteristic of the 3‐substituted cyclohexanols, and this fact has been conclusively verified by the unambiguous synthesis of the axial and equatorial epimers of 3‐(2,2, exo‐3‐trimethyl‐exo‐5‐norbornyl)‐cyclohexanol.
Published Version
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