EP0000771B1 - 2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes - Google Patents

2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes Download PDF

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Publication number
EP0000771B1
EP0000771B1 EP19780100580 EP78100580A EP0000771B1 EP 0000771 B1 EP0000771 B1 EP 0000771B1 EP 19780100580 EP19780100580 EP 19780100580 EP 78100580 A EP78100580 A EP 78100580A EP 0000771 B1 EP0000771 B1 EP 0000771B1
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EP
European Patent Office
Prior art keywords
dimethyl
olfactory
preparation
methyl
trimethyl
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Expired
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EP19780100580
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German (de)
English (en)
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EP0000771A2 (fr
EP0000771A3 (en
Inventor
Paul Albert Dr. Ochsner
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Givaudan SA
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L Givaudan and Co SA
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Priority claimed from LU77923A external-priority patent/LU77923A1/de
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Publication of EP0000771A3 publication Critical patent/EP0000771A3/xx
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
    • C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups

Definitions

  • the invention relates to new fragrances, namely compounds of the formula wherein R represents the 1-hydroxy-2-methyl-propyl or the 3-hydroxy-butyl radical.
  • Formula I accordingly comprises 2,5,7-trimethyloctan-3-01 (la) and 2,4-dimethyl-nonan-8-ol (Ib).
  • Chloride, bromide and iodide are suitable as halide; bromide and chloride are particularly suitable.
  • Raney nickel and palladium are expediently suitable as catalysts.
  • the octanone can also be reduced to alcohol using sodium borohydride or lithium aluminum hydride (L.F. Fieser & M. Fieser, Reagents for Organic Synthesis, John Wiley & Sons 1967, 582, 1049).
  • 1,4-octadienone it is expedient first to work at room temperature in order first to hydrogenate the double bonds, and then - for the purpose of hydrogenating the keto group - at elevated temperature.
  • This latter hydrogenation can e.g. at temperatures of 120-150 ° C, especially at about 140 ° C.
  • nonenol it is preferred to start with material prepared in situ, which is accessible, for example, by catalytic hydrogenation from 6,8-dimethyl-3-nonen-2-one using copper chromite.
  • the 3,5-nonadienone is also preferably hydrogenated using copper chromite.
  • the nonanone is expediently reduced to the alcohol Ib using sodium borohydride or lithium aluminum hydride.
  • the 2,4-dimethylpentyl halides required for process variant a) can be obtained by adding hydrogen halide to 2,4-dimethyl-1-pentene according to methods known per se - in the presence of a peroxide - or by replacing the primary alcoholic grouping of 2,4- Dimethylpentanol - also in a manner known per se by means of phosphorus halides - accessible.
  • 2,5,7-trimethyl-1,4-octadien-3-one is known, for example, from 2,4,7-trimethyl-7-octen-5-yn-4-ol by propargylic rearrangement Way with the help of a vanadium catalyst - possible.
  • Catalytic hydrogenation of the dienone obtained at room temperature - as described above - makes 2,5,7-trimethyl-3-octane p n accessible.
  • the 6,8-dimethyl-3-nonen-2-one is accessible, for example, by aldol condensation of 3,5-dimethylhexanal with acetone.
  • the alcohols I have special organoleptic properties which make them particularly suitable as fragrances.
  • the invention accordingly also relates to the use of I, in particular in the form of mixtures, as fragrances, and fragrance compositions which are characterized by a content of these alcohols I.
  • the compound la used as a fragrance according to the invention is distinguished by interesting fruity (apricot-like) smell nuances.
  • the alcohol Ib on the other hand, is characterized by a pleasantly floral, fruity, earthy green, mushroom note, whereby aldehydic secondary notes can be identified.
  • the compounds can accordingly serve, for example, for perfuming products such as cosmetics (soaps, mouthwashes, deodorants, shampoos, lotions, ointments, powders, etc.), detergents, etc., the compounds preferably not alone, but in the form of compositions other fragrances are used.
  • 2,5,7-trimethyi-octan-3-oi produces a velvety, rounded effect in bouquets of various directions, which can be much more important than the apricot-like odor.
  • 2,4, -dimethyl-nonan-8-ol which has an earthy, natural note, its addition in compositions achieves considerable reinforcement and a radiance that is particularly noticeable in rose and jasmine notes. Since the new compounds are also saturated alcohols, they are extremely stable in mixtures.
  • Compounds I are suitable as fragrances because of their high harmonic insertion capacity, in particular in combination with a number of natural fragrances, e.g. Galbanum oil, vetiver oil, patchouli oil, cedarwood oil, bergamot oil, spruce needle oil, petitgrain oil, tree moss, lemon oil, coriander oil, angelica seed oil, cardamom oil.
  • natural fragrances e.g. Galbanum oil, vetiver oil, patchouli oil, cedarwood oil, bergamot oil, spruce needle oil, petitgrain oil, tree moss, lemon oil, coriander oil, angelica seed oil, cardamom oil.
  • Compound la can also be used advantageously in mixtures with mastic oil, palmarosa oil, jasmine absolute, mandarin oil and hyssop oil, while compound Ib, on the other hand, produces desired effects with ylang-ylang oil.
  • the compounds Ia and Ib can accordingly be used in the production of compositions and - as the production above shows - using a wide range of known odoriferous substances, in particular for the production of compositions with fruity, floral, green, woody, chyper-like and cologne-like notes.
  • Alcohol Ib has a natural, mushroom-like odor that is reminiscent of damp forests. Because of this property, Ib, for example in jasmine or rose compositions, significantly enhances the desired natural character of the perfume. The radiance that the compound Ib gives to compositions is particularly valuable in the production of Compositions used in industrial perfumery, such as perfuming soaps and washing powders.
  • the concentration of the compounds I can vary within wide limits, for example between about 0.01 (detergents) and about 15% by weight (alcoholic solutions).
  • concentrations can of course also be higher.
  • the perfume bases can be used in the usual way for perfuming Eaux de Cologne, Eaux de toilette, lotions, creams, shampoos, soaps and detergents, etc.
  • n D 20 1.4736
  • 64 g of the ketone are hydrogenated in a stirred autoclave in the presence of 6 g of copper chromite under a hydrogen pressure of 40 bar.
  • the temperature is first brought to 140 ° C.
  • the hydrogen absorption ceases (after 3 hours)
  • the mixture is heated to 170 ° C. and kept between 165 and 170 ° C. for 3 hours.
  • the catalyst is filtered off with suction and distilled.
  • 65 g of chemically pure 2,4-dimethyl-nonan-8-ol are obtained (yield: 85.4%).
  • This composition probably has the character of a lily of the valley and targets lilac; for the time being, however, it appears synthetic and somewhat aggressive. After adding 100 parts by weight of 2,5,7-trimethyl-octan-3-ol there is a velvety impression, the note now appears rounded and fruity.
  • this composition has a fruity character; the addition of 2,5,7-trimethyloctan-3-ol strengthens and improves the fruity note in the direction of apricots, the natural effect of ripe apricots is achieved.
  • the 100 parts by weight of 2,5,7-trimethyloctan-3-ol impart a natural, rounded character to the mixture, the typical note of the ripe melon is more recognizable.
  • This floral base is particularly suitable for perfuming soaps and washing powders. With a dosage of 1 to 1.5% by weight in soaps, the composition behaves like an extremely stable, powerful perfume. In washing powders, the optimal effect is obtained at a dosage of 0.1 to 0.3%; the floral note is particularly emphasized by the presence of 2,4-dimethyl-nonan-8-ol.
  • This composition represents an "ordinary" rose composition. If you now add 145 parts by weight of 2,4-dimethyl-nonan-8-ol, you get a base with much more volume, which looks more natural and especially on rose petals and on the "Rose de mai "(cross between Rosa centifolia and Rosa gallica).
  • This classic chypre base is clearly improved by adding 100 parts by weight of 2,4-dimethyl-nonan-8-ol, creating a floral and green shade and enhancing the (desired) smell of undergrowth.
  • the conventional lilac composition gets an earthy shade, which makes the otherwise “synthetic" smell more balanced, flowery, more natural.
  • the new alcohol has a rounded effect.
  • the composition with the new alcohol appears less “sharp”, but more powerful, it is much more suitable for perfumery.

Claims (3)

1. Procédé de préparation de composés de formule
Figure imgb0020
où R représente le radical 1-hydroxy-2-méthyl-propyle ou le radical 3-hydroxy-butyle, caractérisé en ce que, ou bien
a) On fait réagir du 3,5-diméthylhexanal avec un halogénure d'isopropylmagnésium ou de l'isobutyraldéhyde avec un halogénure de 2,4-diméthylpentylmagnésium, ou
b) On hydrogène du 2,5,7-triméthyl-4-octén-3-ol, ou du 6,8-diméthyl-3-nonén-2-ol ou de la 2,5,7-triméthyl-1,4-octadién-3-one ou de la 6,8-diméthyl-3,5-nonadién-2-one ou encore de la 2,5,7-triméthyl-3-octanone ou de la 6,8-diméthyl-2-nonanone.
2. Composition odoriférante, caractérisée en ce qu'elle contient un composé de formule
Figure imgb0021
où R représente le radical 1-hydroxy-2-méthylpropyle ou le radical-3-hydroxy-butyl.
3. Composés de formule
Figure imgb0022
où R représente le radical 1-hydroxy-2-méthylpropyle ou le radical 3-hydroxybutyle.
EP19780100580 1977-08-04 1978-08-02 2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes Expired EP0000771B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
LU77923A LU77923A1 (de) 1977-08-04 1977-08-04 Verfahren zur herstellung eines neuen riechstoffes
LU77923 1977-08-04
CH653778 1978-06-15
CH6537/78 1978-06-15

Publications (3)

Publication Number Publication Date
EP0000771A2 EP0000771A2 (fr) 1979-02-21
EP0000771A3 EP0000771A3 (en) 1979-06-27
EP0000771B1 true EP0000771B1 (fr) 1981-09-16

Family

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EP19780100580 Expired EP0000771B1 (fr) 1977-08-04 1978-08-02 2,5,7-Triméthyloctane-3-ol et 2,4-diméthylnonane-8-ol; procédés pour leur préparation, leur emploi comme agents odorants; compositions odorantes les contenant, ainsi que la préparation de telles compositions odorantes

Country Status (7)

Country Link
US (1) US4198532A (fr)
EP (1) EP0000771B1 (fr)
JP (1) JPS5427506A (fr)
DE (2) DE2861081D1 (fr)
FR (1) FR2399240A1 (fr)
GB (1) GB2001984B (fr)
NL (1) NL7808230A (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6058209B2 (ja) * 1978-12-01 1985-12-19 エーザイ株式会社 β，γ−ジヒドロポリプレニルアルコ−ルおよびそれからなる血圧降下剤
ATE14489T1 (de) * 1980-03-13 1985-08-15 Square D Starkstrom Gmbh Elektromagnetisches schuetz.
US4420423A (en) * 1980-10-09 1983-12-13 International Flavors & Fragrances Inc. Methyl substituted-2-oxohexane derivatives and process for preparing and using same
US4335009A (en) * 1980-06-19 1982-06-15 International Flavors & Fragrances Inc. Mixture of aliphatic C10 branched olefin epoxides and use thereof in augmenting or enhancing the aroma of perfumes and/or articles
US4532361A (en) * 1980-06-19 1985-07-30 International Flavors & Fragrances Inc. Methyl substituted-2-oxohexane derivatives and processes for preparing and using same
US4421679A (en) * 1980-10-09 1983-12-20 International Flavors & Fragrances Inc. Methyl substituted-2-oxohexane derivatives and processes for preparing and using same
US4406810A (en) * 1981-07-06 1983-09-27 International Flavors & Fragrances Inc. Use of Prins reaction products of diisobutylene in augmenting or enhancing the aroma of detergents
GB0916363D0 (en) * 2009-09-18 2009-10-28 Givaudan Sa Organic compounds
EP2857482B1 (fr) 2012-06-01 2017-10-11 Kao Corporation Composition de parfum
JP5709969B1 (ja) 2013-11-29 2015-04-30 花王株式会社 香料組成物
CN112334567A (zh) * 2018-05-31 2021-02-05 丝趣科尔卡有限公司 气味剂仲醇及其组合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838576A (en) * 1958-06-10 Tertiary alcohols
US3125605A (en) * 1964-03-17 Process for the production of alcohols
US3308172A (en) * 1962-08-22 1967-03-07 Koppers Co Inc Asymmetric synthesis of alcohols
US3910897A (en) * 1972-04-21 1975-10-07 Hoffmann La Roche Pest retardants
US3833635A (en) * 1972-06-23 1974-09-03 Zoecon Corp 2,4-diene thiolesters and acids
CH583672A5 (fr) * 1974-03-15 1977-01-14 Givaudan & Cie Sa
NL7602686A (nl) * 1976-03-15 1977-09-19 Naarden International Nv Werkwijze ter bereiding van parfumcomposities ter bereiding van als parfumgrondstof bruikbare nieuwe alkadieenderivaten alsmede geparfumeerde voorwer- pen.

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Publication number Publication date
EP0000771A2 (fr) 1979-02-21
JPS5427506A (en) 1979-03-01
DE2861081D1 (en) 1981-12-03
GB2001984B (en) 1982-01-27
GB2001984A (en) 1979-02-14
NL7808230A (nl) 1979-02-06
EP0000771A3 (en) 1979-06-27
FR2399240A1 (fr) 1979-03-02
JPS636532B2 (fr) 1988-02-10
US4198532A (en) 1980-04-15
DE2833885A1 (de) 1979-02-15

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