International Flavors & Fragrances Inc.

William J Evers

Howard H Heinsohn, Jr

Manfred H Vock

Braja D Mookherjee

Augustinus G Van Loveren

Anton Van Ouwerkerk

Christopher Giacino

Gilbert Stork

Alfred E Goossens

Richard A Wilson

Ira Katz

Bernard J Mayers

Frederick L Schmitt

Joaquin F Vinals

Jacob Kiwala

Edward J Shuster

Alan O Pittet

Igor A Pelse

William L Schreiber

Donald A Withycombe

Michael J Zampino

Bernard J Chant

Michel Van Praag

Anne Sanderson

Elizabeth A Karoll

Gerard Joseph Mosciano

Barja D Mookherjee

Bernard J Rutkowsky

Michel Van Praac

Gerrit W Verhoeve

Joseph Sieczkowski

Howard H Heinsohn Jr

Anne Hruza Nee Sanderson

Louis J Strasburger

Described is the novel compound, bicyclo[10.2.0]tetradecan-13-one having the structure: ##STR1## as well as the use thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, cosmetic powders and hair preparations). Also described is a process for preparing said bicyclo[10.2.0]tetradecan-13-one using as a reaction intermediate the compound having the structure: ##STR2##

Bicyclo[10.2.0]tetradecan-13-one, fragrance use thereof, process for

Described are polyalkyl-substituted oxocycloheptane derivatives defined according to the structure: ##STR1## wherein X represents one of the moieties: ##STR2## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond; or both dashed lines are carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 represents hydrogen or lower alkyl with the proviso that when the dashed line at the 4-5 position is a double bond, R.sub.2 is hydrogen and when the dashed line at the 3-4 position is a double bond, R.sub.1 is hydrogen; wherein R.sub.4 represents C.sub.1 -C.sub.4 lower alkyl; and wherein Y represents chloro or bromo. Also described are the organoleptic uses of said polyalkyl-substituted oxocycloheptane derivatives in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid aninonic, cationic, nonionic or zwitterionic detergents, fabric softener articles, fabric softener compositions and perfumed polymers. Also described are the processes for preparing said polyalkyl-substituted oxocycloheptane derivatives.

Polyalkyl-substituted oxocycloheptane derivatives, organoleptic uses

Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide with a substituted or unsubstituted prenyl ester having the structure: ##STR2## wherein R.sub.3 represents C.sub.1 -C.sub.5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form a halogen-ester intermediate defined according to the structure: ##STR3## then dehydrohalogenating said halogen-ester intermediate using an alkali metal carbonate and a dimethylformamide solvent in order to form a ketoester having the structure: ##STR4## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the ketoester in the presence of an alkali metal carbonate and dimethylformamide solvent in order to form the triconjugated dienone.

Synthesis of triconjugated dienones and novel intermediates used in said

Described are organoleptic utilities of mixtures of t-mercapto terpene isomers defined according to the generic structure: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond taken further together with .alpha.-terpineol having the structure: ##STR2## .beta.-phenylethyl alcohol having the structure: ##STR3## 3-methyl-1-phenyl-pentanol-5 having the structure: ##STR4## and/or butanoyl cyclohexane derivatives defined according to the generic structure: ##STR5## wherein one of the dashed lines is a carbon-carbon double bond or two of the dashed lines represent carbon-carbon double bonds but that when two of the dashed lines represent carbon-carbon double bonds, the carbon-carbon double bonds are conjugated.

Mixtures of one or more t-mercapto terpene isomers and

Described are mixtures of t-mercapto terpene isomers defined according to the generic structure: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond taken further together with .alpha.-terpineol having the structure: ##STR2##

Mixture of one or more t-mercapto terpene isomers and .alpha.-terpineol

Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: ##STR4## then dehydrohalogenating the compound defined according to the structure: ##STR5## using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: ##STR6## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the compound having the structure: ##STR7## in order to form the compound having the structure: ##STR8## the dehydroacyloxylation step taking place in the presence of an akali metal carbonate and dimethylformamide solvent.

Synthesis of triconjugated dienones and intermediates used in said

Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: ##STR4## then dehydrohalogenating the compound defined according to the structure: ##STR5## using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: ##STR6## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydrocyloxylating the compound having the structure: ##STR7## in order to form the compound having the structure: ##STR8## the dehydroacyloxylation step taking place in the presence of an alkali metal carbonate and dimethylformamide solvent.

Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol by first reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## in order to produce the ketone defined according to the structure: ##STR4## which is hydrogenated to form the compound having the structure: ##STR5## and further hydrogenated to form the ketone having the structure: ##STR6## This ketone is reacted with CH.sub.3 M wherein M represents Li or MgX and wherein X is chloro, bromo or iodo to form the organometallic intermediate defined according to the structures: ##STR7## These compounds are then hydrolyzed with dilute acid to form the organoleptically useful 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol isomers of our invention defined according to the structures: ##STR8##

1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, process for

Described is a process for preparing a mixture of t-mercapto terpenes defined according to the structure: ##STR1## and .alpha.-terpineol defined according to the structure: ##STR2## including the step of reacting the compound defined according to the structure: ##STR3## with an alkali metal thiocyanate defined according to the structure: ##STR4## wherein M represents alkali metal such as sodium, potassium or lithium in the presence of a phase transfer catalyst. The resulting product is then treated with lithium aluminum hydride followed by aqueous mineral acid to form a mixture of .alpha.-terpineol and the compound defined according to the structure: ##STR5## which mixture is useful for its organoleptic properties.

Process for preparing mixtures containing 8,9-epithio-1-p-menthene

Described is a novel process for preparing 1,2,3,3,5,6-hexamethyl- bicyclo [2,2,2.] oct-5-en-2-ol by using 2,6,6-trimethylcyclohexa-2,4-diene-1-one as a starting material.

1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol, and organoleptic

Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes.

Process for augmenting or enhancing aroma of consumable material by

Described is a process for augmenting or enhancing the aroma of a perfumed article which is a solid or liquid anionic, cationic, nonionic or zwitterionic detergent or a fabric softener composition or a dryer-added fabric softener article comprising the step of adding to said perfumed article at least one compound having a structure selected from the group consisting of: ##STR1##

Process for augmenting or enhancing the aroma of perfumed articles by

Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes.

1,2,3,3,5,6-Hexamethyl-bicyclo[2.2.2]-oct-5-en-2-ol, process for

Described is 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol as a mixture of isomers and in its isomeric forms having the structures: ##STR1## and the uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles, and colognes. Also described is a novel process for preparing 1,2,3,3,5,6-hexamethyl-bicyclo[2.2.2]oct-5-en-2-ol.

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Red Bank, NJ, United States of America

William J Evers