Firmenich Sa

Karl-Heinrich Schulte-Elte

Gunther Ohloff

Herve Pamingle

Wolfgang K Giersch

Christian Vial

Werner Skorianetz

Walter Renold

Christian Chapuis

Bernard L Muller

Christian Margot

Roger L Snowden

Michel Joyeux

Arnold Hauser

Claudio Tarchini

Bruno Willhalm

Beatrice Baer

Fritz Gautschi

Peter Fankhauser

Joseph J Becker

Hugo Strickler

Dietrich Kastner

Pierre-Alain Blanc

Daniel Reichlin

Cyril Mahaim

Dana P Simmons

Henri Jindra

Richard C Cookson

Herv&eacute; Pamingle

Fritz Gautschl

Bernard Egger

Bernard M/u/ Ller

The present invention relates to perfumery of compounds of the general formula

Perfuming ingredients of woody, fruity odor

The optically active compounds of formula ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl radical, or of formula ##STR2## are useful as perfuming ingredients for the preparation of perfuming compositions and perfumed articles to which they impart woody-amber notes.

Optically active aliphatic alcohols and their use as perfuming

The present invention relates to the use in perfumery of compounds of the general formulae ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent each a methyl or ethyl group, R.sup.3 represents hydrogen or an alkyl group from C.sub.1 to C.sub.4, linear or branched, and R.sup.4 represents hydrogen, an alkyl group from C.sub.1 to C.sub.4, linear or branched, or an acyl group of formula R.sup.5 C(O)--, R.sup.5 being hydrogen or an alkyl group from C.sub.1 to C.sub.4, linear or branched. The novel odoriferous character of these compounds is the combination of woody with fruity notes. Also described is a synthesis for the preparation of the compounds of formula (I) starting from the compounds of formula (II).

The compounds of the formula ##STR1## wherein R represents a 3,3-dimethyl-1-cyclopentyl or a 3,3-dimethyl-1-1cyclohexyl radical, R.sup.5 represents a saturated, linear or branched, C.sub.1 to C.sub.3 alkyl radical and, either R.sup.1 and R.sup.2 stand each for a hydrogen atom, R.sup.3 and/or R.sup.4 representing a methyl radical, or R.sup.3 and R.sup.4 represent each a hydrogen atom, R.sup.1 and/or R.sup.2 representing then a methyl radical, are novel compounds and useful perfuming ingredients, capable of imparting to the compositions into which they are incorporated odor notes of the musky-ambrette and fruity type. A process for the preparation of compounds (I) is disclosed.

Esters and their use in perfumery

Process for the preparation of polycyclic ethers of formula ##STR1## wherein X represents --(CH.sub.2).sub.n --, index n stands for integer 0 or 1, symbol R.sup.4 designated a hydrogen atom or a methyl radical, R.sup.2 identical or different, represent each a hydrogen atom or a lower alkyl radical from C.sub.1 to C.sub.3 and R designates either a C.sub.1 to C.sub.6 linear or branched alkyl radical, or a substituted or unsubstituted alkenyl radical having 2 or 3 carbon atoms in the main chain, said alkenyl radical forming a ring such as indicated by the dotted line, which process comprises the cyclization by means of an acidic agent of an unsaturated compound:

Preparation of polycyclic ethers

Process for the preparation of polycyclic ethers of formula ##STR1## wherein X represents --(CH.sub.2).sub.n --, index n stands for integer 0 or 1, symbol R.sup.4 designates a hydrogen atom or a methyl radical, symbols R.sup.1 and R.sup.2, identical or different, represent each a hydrogen atom or a lower alkyl radical from C.sub.1 to C.sub.3 and R designates either a C.sub.1 to C.sub.6 linear or branched alkyl radical, or a substituted or unsubstituted alkenyl radical having 2 or 3 carbon atoms in the main chain, said alkenyl radical forming a ring such as indicated by the dotted line, which process comprises the cyclization by means of an acidic agent of an unsaturated compound:

Spiro[5.7]tridec-1-ene-3-one is a useful perfuming ingredient for the preparation of perfuming bases and perfumed articles to which it imparts odor notes of the costus, animal and leather type.

Use of a spiranic compound as a perfuming ingredient

Novel compounds of formula ##STR1## wherein the dotted lines indicate the location of a single or double bond, symbol R.sup.1 stands for a hydrogen atom or a methyl radical, symbol R.sup.2 represents a linear or branched, saturated or unsaturated, C.sub.1 to C.sub.4 alkyl radical, provided that R.sup.1 is not hydrogen when R.sup.2 represents a methyl or n-propyl radical and the ring is saturated. Compounds (Ia) are useful as perfuming ingredients. A process for their preparation is disclosed.

Cyclic ketones and their use as perfuming ingredients

New 4,4,5,8-tetramethyl-1-oxaspiro[2,5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described. 4,4,5,8-Tetramethyl-1-oxaspiro[2,5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthesis of valuable fragrance ingredients.

2,2,3,6-tetramethyl-cyclohexane-carbaldehyde

Process for the preparation of polycyclic ethers of formula ##STR1## wherein X represents --(CH.sub.2).sub.n --, index n stands for integer 0 or 1, symbol R.sup.4 designates a hydrogen atom or a methyl radical, symbols R.sup.1 and R.sup.2, identical or different, represent each a hydrogen atom or a lower alkyl radical from C.sub.1 to C.sub.3 and R designates either a C.sub.1 to C.sub.6 linear or branched alkyl radical, or a substituted or unsubstituted alkylene radical having 2 or 3 carbon atoms in the main chain, said alkylene radical forming a ring such as indicated by the dotted line, which process comprises the cyclization by means of an acidic agent of an unsaturated compound:

Process for the preparation of polycyclic ethers

New 4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described. 4,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthetis of valuable fragrance ingredients.

Tetramethyl-1-oxaspiro[2.5]octane

Oxygen containing macrocyclic compounds of formula ##STR1## wherein (a) the dotted lines indicate the location of an endocyclic single or double bond in positions 4 and 8 of the ring and of an exocyclic carbon-oxygen single bond in position 1, the wavy lines define a C--C bond of E or Z configuration when the bond in positions 4 and 8 is a double bond, and the symbols Z.sup.1 and Z.sup.2, taken together, define a cyclic acetal or ketal group represented by the formula ##STR2## wherein the symbols R.sup.1 and R.sup.2, identical or different, represent each an alkyl radical, linear or branched, containing from 1 to 6 carbon atoms, or one of said symbols represents a hydrogen atom and the other an alkyl radical defined as above; or wherein

Oxygen containing macrocyclic compounds, a process for their preparation

The bicyclic ester represented by the formula ##STR1## or 2-(2,3,4,5,6,7-hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl acetate, develops odor characters of the woody, slightly amber and musky type, and can therefore be advantageously used for the preparation of perfuming compositions or perfumes, and for perfuming products such as soaps, cosmetic preparations, detergents, fabric softeners or air deodorizers.

Perfuming ingredient

2,3-Epoxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone, an epoxy ketone of formula ##STR1## possess useful fragrance characters and, consequently, it can be used advantageously in the manufacture of perfume, perfume bases and perfumed products. It develops a flowery and fruity odor.

Unsaturated aliphatic ketone and use of same as perfuming ingredient

2,3-Epoxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone, an epoxy ketone of formula ##STR1## possesses useful fragrance characters and, consequently, it can be used advantageously in the manufacture of perfume, perfume bases and perfumed products. It develops a flowery and fruity odor.

Growing community of inventors

Onex, Switzerland

Karl-Heinrich Schulte-Elte