International Flavors & Fragrances Inc.

Braja Dulal Mookherjee

Edward J Shuster

Manfred H Vock

Venkatesh Kamath

Robert W Trenkle

Joaquin F Vinals

Kenneth K Light

Carlos Benaim

Ramanlal Ranchodji Patel

Processes and compositions are described for altering the aroma of consumable products including perfumes, perfume compositions and perfumed articles utilizing as the essential ingredient one or more of the polycycloalkyl oxyalkanes and/or oxyalkenes (broadly hereinafter referred to as polycycloalkyl oxyhydrocarbons) having the generic formula: ##STR1## the polycyclic moiety being bicyclic or tricyclic, wherein X is one of the moieties: ##STR2## provided that the polycyclic moiety is tricyclic only when X contains an epoxide moiety; and wherein one of the dashed lines is a carbon-carbon bond and each of the wavy lines is a carbon-carbon single bond, one of the carbon-carbon single bonds represented by the wavy line being epimeric with respect to the other of the carbon-carbon single bonds represented by the wavy line; and processes for preparing individual compounds or mixtures of these compounds including the steps of:

Photochemical preparation of polycycloalkyl oxyalkanes and oxyalkenes

Described are the novel compounds, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanol and 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanol, and processes for preparing the aforementioned alcohols and acetate esters thereof.

Novel compounds, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanol

Described is a genus of novel compounds, defined by the generic structure: ##SPC1## Wherein n is 0 or 1 and X is selected from the group consisting of 1,2-cyclo-propylene having the structure: ##SPC2## And 1,2-ethenylene having the structure: ##SPC3## X being cyclopropylene when n is 1, useful for altering, enhancing, modifying or imparting an aroma of or to consumable products including perfumes, perfume comositions and perfumed articles.

Tetracyclic alcohols

Described is a process comprising adding to tobacco itself, or to homogenized or reconstituted tobacco (for subsequent incorporation into smoking articles along with tobacco blend) an amount sufficient to alter the flavor or aroma of the ultimate tobacco mixture of 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanone and/or 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanone.

Tobacco article comprising a flavoring composition selected from

Described is a process comprising adding to homogenized or reconstituted tobacco (for subsequent incorporation into smoking articles along with tobacco blend) an amount sufficient to alter the flavor or aroma of the ultimate tobacco mixture of tricyclene-9-butenone (1,7-dimethyl-7(1-pent-2-en-4-onyl) nortricyclene) having the structure: ##SPC1##

Tobacco article comprising the flavoring composition

A process for the preparation of a mixture of compounds of the structure ##SPC1## Is disclosed whereby a Pi-halotricyclene having the structure ##SPC2## Where Y is chloro, bromo or iodo is reacted with an alkali metal cyanide to prepare the corresponding nitrile; the nitrile is reacted with diisobutylaluminum hyhdride to prepare the corresponding aldehyde, a nortricycloekasantalal which is then condensed with butanone to prepare the above mentioned mixture of compounds. Also claimed are the product ketones which are useful for altering the aroma of consumable products including perfumes, perfume compositions and perfumed articles.

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Matawan, NJ, United States of America

Braja Dulal Mookherjee