International Flavors & Fragrances Inc.

John B Hall

Manfred H Vock

Mark A Sprecker

Joaquin F Vinals

Edward J Shuster

Frederick L Schmitt

Braja D Mookherjee

James M Sanders

William L Schreiber

Venkatesh Kamath

Ching Y Tseng

Kenneth K Light

Denis E Hruza, Sr

Takao Yoshida

Denis E Hruza

Wilhelmus J Wiegers

Jacob Kiwala

Robert M Novak

William I Taylor

Robert W Trenkle

Edward J Granda

James N Siano

Robin L Kasper

Ronald P Schreck

Ronald Schreck

Ira D Hill

John J Kryschuk

Richard A Wilson

Gilbert Stork

Wilhelmus Johannen Weigers

Marie R Hanna

Robert P Belko

Augustinus G Van Loveren

Joseph A McGhie

Chi-Kuen Shu

Edward J Schuster

Described are the 2-isopropenyl-5-methylcyclopentanealkanols and esters thereof having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.2 -C.sub.3 acyl and wherein n represents 0 or 1 and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, cosmetic compositions, fabric softener compositions, fabric softener articles and hair preparations.

2-isopropenyl-5-methylcyclopentanealkanols derivatives and organoleptic

Described are 2-methyl-4-phenyl-1-pentanol derivatives defined according to the structure: ##STR1## wherein R represents hydrogen or acetyl and uses thereof in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, medicinal products and chewing tobaccos.

Uses of methyl phenyl pentanol derivatives in augmenting or enhancing

2-isopropenyl-5-methylcyclopentanealkanols, esters thereof and

Described is a novel genus of compounds defined according to the structure: ##STR1## wherein Z represents hydrogen, MgX and the moiety having the structure: ##STR2## and X represents chlor, bromo, or iodo; as well as 5-isopropyl-8-methyl-5,8-nonadien-2-one; uses of same as intermediates in a process for producing isosolanone and solanone; and organoleptic uses of 5-isopropyl-8-methyl-5,8-nonadien-2-one and 2,6-dimethyl-5-methylene-1-hepten-4-ol. The novel process of our invention involved the steps of:

Process for the production of isosolanone and solanone, intermediates

Described are tertiary pentamethylindanol derivatives defined according to the structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and uses thereof in augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, foodstuffs, smoking tobaccos and smoking tobacco compositions.

Tertiary pentamethylindanol derivatives and organoleptic uses thereof

Described are tertiary pentamethylindanol derivatives defined according to the structure: ##STR1## wherein the dashed line represents a carbon-carbon single or a carbon-carbon double bond and uses thereof in augmenting or enhancing the aroma or taste of smoking tobaccos or smoking tobacco compositions.

Use of pentamethylindanol derivatives in augmenting or enhancing the

Described is a novel genus of compounds defined according to the structure: ##STR1## wherein Z represents hydrogen, MgX and the moiety having the structure: ##STR2## and X represents chloro, bromo or iodo; as well as the novel compounds defined according to the structures: ##STR3## and mixtures of same shown according to the structure: ##STR4## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond; uses of same as intermediates in a process for producing isosolanone which is a mixture of compounds having the structures: ##STR5## or shown by the single structure: ##STR6## and solanone which is a mixture of compounds having the structures: ##STR7## or shown by the structure: ##STR8## wherein the wavy lines are indicative of a cis or trans juxtaposition of the hydrogen or 2-propenyl moieties about the double bond; and organoleptic uses of the compounds having the structures: ##STR9##

Isosolanone and solanone intermediates and organoleptic uses

Described are 1-oxoalkyl-2-isopropylnorbornane derivatives defined according to the generic structure: ##STR1## wherein X represents a moiety selected from the group consisting of: ##STR2## wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond and wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that R.sub.1 and R.sub.2 are not both methyl, and uses thereof in augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, colognes and perfumed articles. Also described are processes for preparing said 1-oxoalkyl-2-isopropylnorbornane derivatives by means of a low temperature catalytic Diels Alder reaction or high temperature thermal Diels Alder reaction between a bicyclopentadiene derivative and 2-methyl-3- buten-5-one according to the reaction: ##STR3## wherein R represents methyl or hydrogen.

1-Oxoalkyl-2-isopropylnorbornane derivatives, uses thereof in augmenting

Flavoring with tertiary pentamethylindanol derivatives

Described is a process for preparing the compound having the structure: ##STR1## comprising the steps of reacting 1-acetyl-3,3-dimethylcyclohexane having the structure: ##STR2## with an alkyl acetate defined according to the structure: ##STR3## wherein R.sub.2 is C.sub.1 -C.sub.5 alkyl such as methylethyl, n-propyl, i-propyl, n-butyl, 2-butyl and tertiary butyl, thereby forming a diketone having the structure: ##STR4## reacting the said diketone with an allyl halide having the structure: ##STR5## (wherein X represents bromo or iodo) to form a substituted diketone having the structure: ##STR6## and then transforming the compound having the structure: ##STR7## into the compound having the structure: ##STR8## by means of a retro-Claisen reaction. Also described is the use in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles of the compound having the structure: ##STR9##

1(1,3-Dioxobutane)-3,3-dimethylcyclohexane useful in perfumes

Use in augmenting or enhancing the aroma or taste of foodstuffs or

Compounds of the following structure ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and 2-propenyl are disclosed useful as intermediates in organic synthesis.

Process for preparing 1(4-pentenoyl)-3,3-dimethylcyclohexane and

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Rumson, NJ, United States of America

John B Hall