International Flavors & Fragrances Inc.

Howard H Heinsohn, Jr

William J Evers

Manfred H Vock

Christopher Giacino

Gilbert Stork

Braja D Mookherjee

Frederick L Schmitt

Bernard J Mayers

Edward J Shuster

Elizabeth A Karoll

Mark A Sprecker

Joaquin F Vinals

Jacob Kiwala

Marie R Hanna

Richard Anthony Weiss

Anthony T Levorse, Jr

Charles E J Beck

Barja D Mookherjee

Described are carbon-containing functional groups substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, process for processes for preparing same, and uses thereof. The 4,5,6,7-tetrahydro-polyalkylated-4-indanes have the generic structure:

Carbon containing functional group substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, processes for preparing same and uses thereof

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 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 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 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## 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 alkali metal carbonate and dimethylformamide solvent.

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 alkali metal carbonate and dimethylformamide solvent.

Described are .alpha.-oxy(oxo) sulfides and ethers having the generic structure: ##STR1## wherein X is one of: ##STR2## Z is one of sulfur or oxygen; when R.sub.1 and R.sub.2 are taken separately, R.sub.1 is hydrogen or methyl, and R.sub.2 is methyl; and when R.sub.1 and R.sub.2 are taken together, R.sub.1 and R.sub.2 form phenyl moeities; and Y is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, acetyl, methoxycarbonylmethyl, or 1,3-diethylacetonyl. Addition of one or more .alpha.-oxy(oxo) sulfides and ethers to foodstuff flavorings or foodstuffs is indicated to produce the following aroma and flavor characteristics, in the alternative or taken together:

.alpha.-Oxy(oxo) sulfides and ethers

Novel 3-furyl alkyl disulfides having the formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.7 lower alkyl or C.sub.5 -C.sub.6 cycloalkyl; R.sub.2 and R.sub.3 are each selected from the group consisting of hydrogen and methyl, at least one of R.sub.2 and R.sub.3 being methyl provided that when R.sub.1 is methyl, each of R.sub.2 and R.sub.3 is methyl, such 3-furyl alkyl disulfides being useful in altering, modifying or enhancing the organoleptic properties of foodstuffs.

3-Furyl alkyl disulfides

Described are .alpha.-oxy(oxo) sulfides and ethers having the generic structure: ##STR1## wherein X is one of: ##STR2## Z is one of sulfur or oxygen; when R.sub.1 and R.sub.2 are taken separately, R.sub.1 is hydrogen or methyl, and R.sub.2 is methyl; and when R.sub.1 and R.sub.2 are taken together, R.sub.1 and R.sub.2 form phenyl moieties; and Y is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, acetyl, methoxycarbonylmethyl, or 1,3-diethylacetonyl. Addition of one or more .alpha.-oxy(oxo) sulfides and ethers to foodstuff flavorings or foodstuffs is indicated to produce the following aroma and flavor characteristics, in the alternative or taken together:

Process for preparing .alpha.-oxy(oxo)sulfides and ethers

Novel 3-furyl alkyl disulfides having the formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.7 lower alkyl or C.sub.5 -C.sub.6 cycloalkyl; R.sub.2 and R.sub.3 are each selected from the group consisting of hydrogen and methyl, at least one of R.sub.2 or R.sub.3 being methyl provided that when R.sub.1 is methy, each of R.sub.2 and R.sub.3 is methyl, such 3-furyl alkyl disulfides being useful in altering the organoleptic properties of foodstuffs.

Flavoring with certain 3-furyl alkyl disulfides

Alpha-oxy(oxo)sulfides and ethers

Processes and compositions are described for the use in foodstuff flavors and as foodstuff aroma and taste augmenting and enhancing materials of 3-propylthio-4-heptanol having the structure: ##STR1##

Growing community of inventors

Hazlet, NJ, United States of America

Howard H Heinsohn, Jr