Givaudan Corporation

Givaudan-roure Corporation

Daniel Helmlinger

Peter Naegeli

Mario Pesaro

Dietmar Lamparsky

Peter Schudel

Jost Wild

Trudi Sigg-Grutter

Franz Etzweiler

Frank Kienzle

Georg Frater

Erich Widmer

Cornelius Nussbaumer

Michael J Klaus

Jean-Pierre Bachmann

The present invention is concerned with novel odorant compositions which are characterized by a content of cyclic compounds of the formula ##STR1## From this group of compounds the compounds I' with the meanings b), d), f) and g) are novel compounds.

Cyclic compounds

A novel process is described for the manufacture of a mixture of 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol (I) and, respectively, of a mixture of [3a.alpha.,5a.beta.,9a.alpha.,9b.beta.]-dodecahydro-3a,6,6,9a-tetramethyln aphtho[2,1-b]furan and [3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.]-dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan, in which E,E-6-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-4-methyl-hexa-2,4-dien-1-al is reduced either with (a) lithium aluminium hydride or with (b) sodium dithionite in the presence of sodium bicarbonate in aqueous solution and of a phase transfer catalyst or with (c) sodium borohydride or with (d) sodium bis(2-methoxyethoxy)aluminium dihydride and, when reduction agent (c) or (d) is used and optionally in the case when reduction agent (a) is used, the E,E-6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hexa-2,4-dien-1-o l which results as the intermediate is reduced to the desired 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol using a reduction agent (a) or (b) and, if desired, the thus-obtained compounds I are converted in a known manner into a mixture of the aforementioned furans. These furans are suitable as odorants.

Process for the manufacture of known odorants

The invention concerns a process for the manufacture of a mixture of (3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)-dodecahydro-3a,6,6,9a-tetramethyln aphtho-[2,1-b]furan and (3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.)-dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan which utilizes the substituted hexenoic acids, 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-2- or -3-enoic acid. The invention also concerns nitriles and a process for manufacture of the hexonic acids from the nitriles, having the formula ##STR1## wherein one of the bonds  denotes a single bond and the other denotes a double bond, and, R represents hydrogen or the ester group COOR.sup.1 in which R.sup.1 represents a lower alkyl or aryl group.

Process for the manufacture of odorants and intermediates used therein

The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5,-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8 -octahydronapthalene.

Acetyl-tri-and-tetramethyl-octahydronaphthalenes and fragrance

The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8- octahydronapthalene.

The present invention concerns the novel odorant 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, I, a process for the manufacture of I, novel intermediates used in the process and fragrance compositions containing I. ##STR1## The process for the manufacture of 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone comprises hydroborating 1,1,2,3,3,6-hexamethyl-4,7-dihydroindane and oxidizing the hydroboration product to 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, or reductively alkylating, especially methylating, 5-nitro-1,1,2,3,3,6-hexamethylindane and converting the resulting 5-dialkyl-amino-1,1,2,3,3,6-hexamethylindane into 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone by reduction of the benzene ring and hydrolysis of the resulting enamine.

1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone and fragrance

A compound of the formula ##STR1## wherein the dotted line signifies an optional bond, as racemates or individual enantiomers, odorant compositions containing the same, and a process for the manufacture of the compounds of formula I which comprises rearranging sclareolide, episclareolide or isosclareolide at an elevated temperature in acidic medium with dehydration and, if desired, reducing the carbon-carbon double bond present in the reaction product.

Tricyclic ketones and fragrance compositions containing same

A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided. ##STR1##

Process for the manufacture of a mixture of .alpha.- and .beta.-irone

A method for the manufacture of the four geometric isomers of 4-(2-butenyl)idene)-3,5,5-trimethy-2-cyclohexen-1-one is provided. The process comprises pyrolyzing a compound of the formula ##STR1## wherein R represents lower-alkyl-oxycarbonyl, aryl-oxycarbonyl, or, preferably, lower-alkanoyl, benzoyl or substituted benzoyl.

Process for the manufacture of

A method for the manufacture of the four geometric isomers of 4(2-butenylidene)-3,5,5-trimethyl-2-cyclohexen-1-one is provided. The process comprises pyrolyzing a compound of the formula ##STR1## wherein R represents lower-alkyl-oxycarbonyl, aryl-oxycarbonyl, or, preferably, lower-alkanoyl, benzoyl or substituted benzoyl.

The invention is concerned with novel bicyclic epoxides, a process for their manufacture and novel fragrance and flavor compositions containing the same.

Novel bicyclic epoxides and compositions

This invention is concerned with novel substituted bicyclo[4.3.0]non-1(6)-en-8-yl methyl ketones, a process for their manufacture and novel fragrance and flavor compositions containing same.

Substituted bicyclo[4.3.0]non-1(6)-en-8-yl methyl ketones and fragrance

Novel odorants, having the formula ##STR1## wherein R represents sec. butyl, tert. butyl or cyclohexyl. A process for preparing the novel odorants from novel intermediates and fragrance compositions containing the odorants are also taught.

2-Substituted-1-acetoxy and hydroxy-1-methyl-cyclohexanes

Novel trimethyl-acetyl-octalins mixtures are prepared by a Diels-Alder-type reaction involving methyl vinyl ketone and compounds having the structure ##STR1## wherein one of the two lines denoted by dots represents an additional bond. The novel compounds possess unique and unexpected desirable olfactory properties.

Growing community of inventors

Gockhausen, Switzerland

Daniel Helmlinger