Novel tricyclic alcohols, novel uses of tricyclic alcohols and processes for preparing same

Abstract

Abstract WHEREIN EACH OF R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is selected from the group consisting of hydrogen and methyl; wherein the dashed line is a carbon-carbon single bond or a carbon-carbon double bond; wherein R1 is limited to hydrogen when (i) the dashed line is a carbon-carbon single bond; (ii) R2, R3, R4, R6, R7, R8, R9 and R10 is hydrogen and (iii) R5 is hydrogen or methyl and wherein when the dashed line is a carbon-carbon single bond, one of R3 or R4 is hydrogen; and processes for preparing the above-mentioned compounds and in addition compounds having similar structures, that is, when the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond; R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each the same or different and each represents hydrogen and wherein when R3 or R4 is hydrogen the dashed line represents a carbon-carbon single bond and when R3 and R4 are both methyl, the dashed line represents a carbon-carbon double bond, involving first intimately admixing a methyl substituted cyclohexadienone having the structure: The ketone may either be immediately cyclized using an alkali metal such as sodium, potassium or lithium in the case of X being halogen, or when X is OH, the ketone is first halogenated with a halogenating agent to first form a compound having the structure: WHEREIN X can be either hydroxyl, bromo or chloro thereby forming a diene compound having the structure: AND THEN HYDROGENATING THE DIENE COMPOUND WITH HYDROGEN IN THE PRESENCE OF A HYDROGENATION CATALYST THEREBY PRODUCING A KETONE HAVING THE STRUCTURE: WHEREIN Y is bromo or chloro and subsequently the halogenated compound may then be cyclized using a cyclizing agent. D R A W I N G WITH AN ACETYLENIC COMPOUND HAVING THE STRUCTURE: D R A W I N G Processes and compositions for altering the flavor and/or aroma of consumable products including foods, tobacco and perfumes utilizing as the essential ingredient at least one organic tricyclic alcohol having the formula:

Inventors

• 👤 Kenneth K Light
• 👤 Edward J Shuster
• 👤 Joaquin F Vinals
• 👤 Manfred Hugo Vock

Bibliographic Details