International Flavors & Fragrances Inc.

Gilbert Stork

Braja D Mookherjee

Manfred H Vock

Frederick L Schmitt

Richard A Wilson

Joaquin F Vinals

Jacob Kiwala

William L Schreiber

William J Evers

Howard H Heinsohn, Jr

Robert W Trenkle

Domenick Luccarelli, Jr

Timothy MacDonald

Arthur L Liberman

John B Hall

Barja D Mookherjee

Arthur L Lieberman

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.

A process is described for the preparation of alkyl and alkylene homologues of methyl dihydrojasmonate which incorporate the novel process step: ##STR1## In the above reaction sequence, X is chloro or bromo and R is C.sub.1 -C.sub.4 alkyl.

Process for the preparation of homologues of methyl dihydrojasmonate

Processes and compositions are described for the use in foodstuff flavor and aroma and perfume and perfumed article aroma augmenting, modifying, altering and enhancing compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of specific isomer and isomer mixtures of 2- and 3-cyclotetradecen-1-ones having the structures: ##STR1## or mixtures of same or mixtures of such 2- and 3-cyclotetradecen-1-ones with cyclotetradecanone having the structure: or cyclododecanone having the structure: ##STR2## Addition of said 2- and 3-cyclotetradecen-1-ones or mixtures is indicated to produce:

Organoleptic uses of 2- and 3-cyclotetradecen-1-ones

Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, smoking tobacco flavor and aroma and perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, smoking tobacco, perfume and perfumed article aroma and/or flavor imparting materials of 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanol and -1,3-cyclohexadiene-1-methanol derivatives or one or more of their geometric or stereoisomers as defined by the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; the dashed line is a carbon-carbon double bond or a carbon-carbon single bond; with the proviso that when R.sub.1 is hydrogen, the dashed line is a carbon-carbon double bond. Addition of one or more of the 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanols or -1,3-cyclohexadiene-1-methanols of our invention to consumable materials is indicated to produce:

2,6,6-Trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanols and

Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, smoking tobacco flavor and aroma and perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, smoking tobacco, perfume and perfumed article aroma and/or flavor imparting materials of 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanol and -1,3-cyclohexadiene-1-methanol derivatives or one or more of their geometric or stereoisomers as defined by the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; the dashed line is a carbon-carbon double bond or a carbon-carbon single bond; with the proviso that when R.sub.1 is hydrogen, the dashed line is a carbon-carbon double bond.

Flavoring with

Described are 2,6,6-trimethyl-alpha-propenyl-1,3-cyclohexadiene-1-methanol substances having the structures: ##STR1## which are useful for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, perfumes, colognes, perfumed articles, smoking tobaccos and smoking tobacco flavors.

2,6,6-Trimethyl-.alpha.-(iso)propenyl-1,3-cyclohexadiene-1-methanols

A process described for the preparation of methyl dihydrojasmonate and lower alkyl homologues according to one of the reaction sequences: ##STR1## The first of the above reaction schemes also incorporates the novel process step: ##STR2## In the above reaction sequence, X is chloro or bromo and R is C.sub.1 -C.sub.4 alkyl.

Process for the preparation of methyl dihydrojasmonate and lower alkyl

Described are processes for augmenting or enhancing the aroma of perfume compositions or colognes, comprising the step of adding in an aroma augmenting or enhancing quantity to a perfume base or a cologne base, one or more compounds defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 are hydrogen; wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond with the proviso that when R.sub.1 is hydrogen, the dashed line represents a carbon-carbon double bond.

2,6,6-Trimethyl-.alpha.-(iso-propenyl-1-cyclohexene-1-methanol and 1,3

Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of adding to a solid or liquid anionic, cationic or nonionic detergent base from 0.005% up to 5% by weight of at least one compound defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond with the proviso that when R.sub.1 is hydrogen, the dashed line represents a carbon-carbon double bond.

Growing community of inventors

Englewood, NJ, United States of America

Gilbert Stork