International Flavors & Fragrances Inc.

Denis E Hruza, Sr

Edward J Shuster

Manfred H Vock

Mark A Sprecker

Braja D Mookherjee

Joaquin F Vinals

John B Hall

William L Schreiber

James M Sanders

Kenneth K Light

Venkatesh Kamath

Ching Y Tseng

Alan O Pittet

Christopher Giacino

John V Pascale

Gary Slangan

Edward J Schuster

Processes and compositions are described for the use in perfume aroma augmenting, enhancing, modifying and imparting compositions and as perfume and perfumed article aroma imparting and enhancing materials of oxyhydrocarbylnorbornanes having the structure: ##STR1## wherein X is carbonyl or carbinyl having the structures, respectively: ##STR2## and wherein at least one of the dashed lines is a carbon-carbon single bond and the other of the dashed lines is a carbon-carbon single bond or a carbon-carbon double bond. Addition of the said oxyhydrocarbylnorbornanes to consumable materials is indicated to produce in perfumes, colognes and perfumed articles, natural, sweet pine, incense, camphene-like, sweet, green, floral, fruity, dried fruity, ionone-like, orris-like and nasturtium-like aromas with dried, woody, piney, sweaty, geranic acid-like nuances.

Method for preparing oxyhydrocarbylnorbornane derivatives

Novel oxyhydrocarbylnorbornane derivatives and perfumery uses thereof

Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of intimately admixing with a solid or liquid cationic, anionic or nonionic detergent base and aroma augmenting or enhancing quantity of at least oxyhydrocarbylnorbornane having the structure: ##STR1## wherein X is carbonyl or carbinyl having the structures, respectively: ##STR2## and wherein at least one of the dashed lines is a carbon-carbon single bond and the other of the dashed lines is a carbon-carbon single bond or a carbon-carbon double bond.

Use of novel oxyhydrocarbylnorbornane derivatives for augmenting or

Perfumery uses of oxyhydrocarbylnorbornane derivatives

Described for use in augmenting or enhancing the organoleptic properties of foodstuffs, chewing gums, toothpastes, medicinal products, tobaccos, perfumes and perfumed articles are one or more hydroxy alkenyl norbornane derivatives having one of the structures: ##STR1##

Hydroxy alkenyl norbornane derivatives

Norbornane derivatives are used in soaps. Specifically, mixture of 2-(2-butenoyl)-3,3-dimethylnorbornane; 2-(3-butenoyl)-3,3-dimethylnorbornane and .alpha.-allyl-3,3-dimethyl-2-norbornanemethanol are used.

Process of enhancing the aroma of a soap with norbornane derivatives

Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste and medicinal product aroma imparting materials of one or more substituted norbornane derivatives or mixtures of the same as follows:

Flavoring with substituted norbornane derivatives

Described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma and perfume aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials are one or more alkenyl or alkylidene norbornyl ketone derivatives having the generic structure: ##STR1## wherein R is C.sub.3 -C.sub.5 alkenyl or C.sub.3 -C.sub.5 alkylidene and the dashed lie is a carbon-carbon single bond or a carbon-carbon double bond, specifically the compounds having the structures: ##STR2## and products produced according to the process of reacting 2-acetyl-3,3-dimethyl-5-norbornene with a complex of N-methylaniline and an alkyl magnesium halide to form a grinard salt of 2-acetyl-3,3-dimethyl-5-norbornene having the structure: ##STR3## said reacting being carried out from -5.degree. C. up to about 40.degree. C.; reacting the resulting compound with acid aldehyde in the presence of a solvent selected from the group consisting of benzene, tetrahydrofuran, and diethyl ether at a temperature in the range of from -5.degree. C. up to 20.degree. C.; hydrolyzing the resulting material to form substantially a keto alcohol in the presence of a mineral acid; and then dehydrating the resulting keto alcohol with a mild dehydrating agent at a temperature in the range of from 80.degree. C. up to 150.degree. C. over a period of time of from 1 up to 5 hours in the presence of a strong acid.

Alkenyl and alkylidene norbornyl ketone derivatives

Compounds of the formula ##STR1## wherein R is ethyl, n-propyl or n-butyl, having organoleptic properties are disclosed.

Alkanoyl dimethylnorbornanes

Norbornane Derivatives are used in foodstuffs and flavorings. Specifically, 3,3-dimethyl-2-pentanoylnorbornane and 2-butyrl-3,3-dimethylnorbornane are used.

A process is disclosed comprising adding a compound, 2-acetyl-3,3-dimethyl-5-norbornene having the structure: ##STR1## to acetaldehyde according to the reaction sequence: ##STR2## whereby a compound having the structure: ##STR3## is formed useful as an organoleptic.

Process for the preparation of butenoyl norbornenes

Disclosed are compounds of the formula ##STR1## wherein the wavy line represents a carbon-carbon single or double bond, possessing organoleptic properties.

Substituted norbornane derivatives

Norbornane derivatives are used in detergents. Specifically, ##STR1## and mixtures of same or a mixture of 2-(2-butenoyl)-3,3-dimethylnorbornane; 2-(3-butenoyl)-3,3-dimethylnorborna ne; 2-(2-butenoyl)-3,3-dimethylnorbornane and alpha-allyl-3,3-dimethyl-2-norbornanemethanol are used.

Process of enhancing the aroma of a detergent with norbornane derivatives

Norbornane derivatives are used in soaps and detergents. Specifically, ##STR1## are used.

Growing community of inventors

Bricktown, NJ, United States of America

Denis E Hruza, Sr