DE2365939C3 - Cyclopentenes, processes for their production and fragrance compositions - Google Patents

Cyclopentenes, processes for their production and fragrance compositions

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Publication number
DE2365939C3
DE2365939C3 DE19732365939 DE2365939A DE2365939C3 DE 2365939 C3 DE2365939 C3 DE 2365939C3 DE 19732365939 DE19732365939 DE 19732365939 DE 2365939 A DE2365939 A DE 2365939A DE 2365939 C3 DE2365939 C3 DE 2365939C3
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DE
Germany
Prior art keywords
cyclopentenes
processes
production
fragrance compositions
woody
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE19732365939
Other languages
German (de)
Other versions
DE2365939A1 (en
DE2365939B2 (en
Inventor
Peter Dr. Wettingen Naegeli (Schweiz)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
L Givaudan and Co SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L Givaudan and Co SA filed Critical L Givaudan and Co SA
Publication of DE2365939A1 publication Critical patent/DE2365939A1/en
Publication of DE2365939B2 publication Critical patent/DE2365939B2/en
Application granted granted Critical
Publication of DE2365939C3 publication Critical patent/DE2365939C3/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/21—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • 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
    • C07C45/513—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 an etherified 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
    • C07C45/51—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
    • C07C45/515—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 an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

R2 R 2

(II)(II)

2020th

2525th

in der R2 die vorstehende Bedeutung besitzt, in an sich bekannter Weise mit Jones-Reagens (CrO3/ H2SO4) oxidiert und die erhaltene Säure der Formelin which R 2 has the above meaning, oxidized in a manner known per se with Jones reagent (CrO 3 / H2SO4) and the acid obtained of the formula

OHOH

(Ia) Untergruppen von erfindungsgemäßen Verbindungen der Formel I werden durch die folgenden Formeln Ia und Ib beschrieben:(Ia) Subgroups of compounds of the formula I according to the invention are represented by the following formulas Ia and Ib described:

30 R2 30 R 2

1010

OHOH

da)there)

OR3 OR 3

(Ib)(Ib)

in denen R2 und die gestrichelt gezeichnete Linie die oben angegebenen Bedeutungen haben und R3 einen niederen Alkylrest darstellt.in which R 2 and the dashed line have the meanings given above and R 3 represents a lower alkyl radical.

Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß man einen Aldehyd der FormelThe process according to the invention is characterized in that an aldehyde of the formula

R2 R 2

(II)(II)

in der R2 die vorstehende Bedeutung besitzt, in an sich bekannter Weise mit Jones-Reagens
oxidiert und die erhaltene Säure der Formelin which R 2 has the above meaning, in a manner known per se with Jones reagent
oxidized and the acid obtained of the formula

in der R2 die vorstehende Bedeutung besitzt, gewünschtenfalls in üblicher Weise mit einem niederen Alkanol verestert.in which R 2 has the above meaning, if desired, esterified in the customary manner with a lower alkanol.

3. Riechstoffkompositionen, gekennzeichnet durch einen Gehalt an einer Verbindung der Formel !gemäß Anspruch 1.3. Fragrance compositions, characterized in that they contain a compound of the formula ! according to claim 1.

Die erfindungsgemäßen Cyclopentene haben die FormelThe cyclopentene according to the invention have the formula

(1)(1)

worin R1 Hydroxy oder eine niedere Alkoxygfup'pe Und R2 Wasserstoff, einen niederen Alkyl' dder niederen Alkylidenrest darstellen und die gestrichelt gezeichnete Linie eine fakultative Bindung bedeutet.wherein R 1 is hydroxy or a lower alkoxy group and R 2 is hydrogen, a lower alkyl or the lower alkylidene radical and the dashed line denotes an optional bond.

In der vorliegenden Anmeldung definiert der Ausdrück »nieder« in Zusammenhang mit Alkyl-, Alkoxy oder AikyÜdenresten Gruppen mit bis zu 6 Köhleflsfoffaforrien,In the present application, the defines The term "lower" in connection with alkyl, alkoxy or AikyÜdenresten groups with up to 6 Köhleflsfoffaforrien,

(Ia)(Ia)

C)C)

in der R2 die vorstehende Bedeutung besitzt, gewünschtenfalls in üblicher Weise mit einem niederen Alkanol verestert.in which R 2 has the above meaning, if desired, esterified in the customary manner with a lower alkanol.

Has Ausgangsmaterial für die Herstellung der erfindungsgem?.Oen Verbindungen kann nach dem Verfahren der DE-OS 23 13 017 hergestellt werden.Has raw material for the manufacture of the Oen compounds according to the invention can be prepared by the process of DE-OS 23 13 017.

Die Verbindungen der Formel I zeichnen sich durch besondere Riechstoffeigenschaften, insbesondere durchThe compounds of the formula I are distinguished by particular odor properties, in particular by

si frische, holzige, campherartige, würzige, teilv/eise auch blumige, esterartige oder schwach süßliche Geruchsnoten aus. Sie können demgemäß als Riechstoffe zur Herstellung von Riechstoffkompositionen, wie Parfüms und Parfümbasen bzw, zur Parfümierung von techni-They are fresh, woody, camphor-like, spicy, partly also floral, ester-like or slightly sweet odor notes. They can accordingly be used as fragrances Production of fragrance compositions, such as perfumes and perfume bases or for perfuming technical

sehen und kosmetischen Produkten aller Art, z< B. von festen und flüssigen Detergentien,'synthetischen W'nseh· mitteln, Aerosolen, Seifen, Cremes oder Lotionen Verwendung finden.see and cosmetic products of all kinds, z < B. of solid and liquid detergents, 'synthetic W'nseh · agents, aerosols, soaps, creams or lotions are used.

Die neuen Ester und Säuren bereichern die Palette des Parfümeurs.The new esters and acids enrich the perfumer's palette.

Der der ganzen Klasse (Säuren, Ester) zukommende Geruchscharakter ist holzig-sOÖlich, hölzig-campherartig bis holzig-erdig-muffig. Bei den Säuren ist dieserThe olfactory character belonging to the whole class (acids, esters) is woody-so-like, woody-camphor-like to woody-earthy-musty. This is the case with acids

Charakter Richtung würzig oder sogar säuerlich modifiziert, bei den Estern treten daneben insbesondere blumige Noten auf. Der holzige Charakter ist aber nicht einfach »holzig« im Sinne von einzelnen Edelholzölen (Sandel) oder den häufig verwendeten Zedern-, Fichtenoder Pinienölen bzw. sogar den Guajak- oder Birkenholzölen (teerig), sondern es liegt eine neuartige, originelle Holznote vor. Auch kann der süßliche, erdige, muffige, champherartige Aspekt nicht einfach den entsprechenden Noten von Patchouliöl, Campheröl oder Vetiveröl gleichgesetzt werden, sondern es sind jeweils eher Kombinationen dieser Noten, die demzufolge auch einen breiten Einsatz der vorliegenden Ester und Säuren ermöglichen.Character modified towards spicy or even sour, with the esters in particular floral notes. The woody character is not simply "woody" in the sense of individual precious wood oils (Sandal) or the frequently used cedar, spruce or pine oils or even the guaiac or Birch wood oils (tarry), but there is a new, original wood note. The sweet, earthy, musty, champagne-like aspect doesn't simply match the corresponding notes of patchouli oil, camphor oil or vetiver oil are equated, but rather they are each rather combinations of these notes, which consequently also a broad use of the present esters and acids.

Die Ester und Säuren liefern originelle Effekte in Riechstoffkompositionen verschiedenster Richtungen, z. B. in Fantasienoten, wie Chypre oder Fougere, in Ambranoten, in Hesperidennoten (Cologne) oder in Blumennoten, wo sie sich z. B. gut mit Ylang-Ylang, Jasmin absolue oder Mimosa absolue verbinden.The esters and acids provide original effects in fragrance compositions in a wide variety of directions, z. B. in fantasy notes such as chypre or fougere, in amber notes, in hesperid notes (Cologne) or in Floral notes where they are z. B. good with ylang-ylang, Connect jasmine absolue or mimosa absolue.

Geeignete Konzentrationen der erfindungsgemäßen Verbindungen sind bei Verwendung als Riechstoff in Parfümkompositionen 1 bis 30%, in Fertigprodukten, wie Shampoos, Seifen oder Lotionen, etwa 0,001 bis 1 %.Suitable concentrations of the compounds according to the invention are when used as a fragrance in Perfume compositions 1 to 30%, in finished products such as shampoos, soaps or lotions, about 0.001 to 1%.

Beispiel 1example 1

Eine Lösung von 25 g 2-(2-Formyläthyl)-3-isopropenyl-l-methyl-cyclopent-l-en in 1200 ml Aceton wurde bei -10° mit 55 ml Jones-Reagens versetzt. Das braune Reaktionsgemisch wurde auf Eis/Natriumbicarbonatlösung gegossen. Ätherextraktion, K ,utralwaschen mit Natriumbicarbonat-, gesättigter Natriumchloridlösung und Wasser, Trocknung des extrakte.· mit Magnesiumsulfat und Entfernung des Lösungsmittels unter vermindertem Druck lieferte 20 g (80%) eines schwach gelben, öligen Rohproduktes, aus dem durch Destillation 15 g reines 2-(2-Carboxyäthyl)-3-isopropenyI-lmethyl-cyclopent-1-en erhalten wurden, Kp.ooi = 102°, IRF,im: vml, = 3600-2400, 1720, 1645. 1450, 1420, 1380, 1330, 1290, 1220, 1085, 945 und 900 cm-'. Die Verbindung hat einen holzigen, würzigen, schwach süßlichen und etwas muffigen Geruch.A solution of 25 g of 2- (2-formylethyl) -3-isopropenyl-1-methyl-cyclopent-1-ene in 1200 ml of acetone was treated with 55 ml of Jones reagent at -10 °. The brown reaction mixture was poured onto ice / sodium bicarbonate solution. Ether extraction, K, ultra-washing with sodium bicarbonate, saturated sodium chloride solution and water, drying of the extract. With magnesium sulfate and removal of the solvent under reduced pressure yielded 20 g (80%) of a pale yellow, oily crude product, from which 15 g of pure 2 - (2-Carboxyethyl) -3-isopropenyl-1-methyl-cyclopent-1-en were obtained, b.p.ooi = 102 °, IRF, im: v ml , = 3600-2400, 1720, 1645, 1450, 1420, 1380, 1330, 1290, 1220, 1085, 945 and 900 cm- '. The compound has a woody, spicy, slightly sweet and somewhat musty odor.

Beispiel 2Example 2

Ein Gemisch aus 2 g 2-(2-Carboxyäthyl)-3-isopropenyl-1-methyl-cyclopent-l-en, 150 ml absolutem Benzol und 4 ml Dimethoxy-dimethylamino-methan wurde 5 Stunden zum Rückfluß erhitzt. Die Lösung wurde eingeengt und der als rotes öl erhaltene Rückstand an 50 g Kieselgel mit Hexan/Äther (19 :1) chromatographiert. Es wurden 1.95 g (91%) 2-(2-Carbomethoxyäthyl)-3-isopropenyl-1 -methyl-cyclopent-1 -en erhalten, Kp.001 etwa 70°, π = 1.4761. IRf,im: vm, = 3100,1742, 1645, 1440. 1375, 1330, 1255, U 95, 1170, 1085, 1025,990, 895 und 840 cm '. Die Verbindung hat einen blumigen, holzigen, esterartigen Geruch.A mixture of 2 g of 2- (2-carboxyethyl) -3-isopropenyl-1-methyl-cyclopent-1-ene, 150 ml of absolute benzene and 4 ml of dimethoxydimethylamino-methane was refluxed for 5 hours. The solution was concentrated and the residue obtained as a red oil was chromatographed on 50 g of silica gel with hexane / ether (19: 1). 1.95 g (91%) of 2- (2-carbomethoxyethyl) -3-isopropenyl-1-methyl-cyclopent-1-ene were obtained, boiling point 001 about 70 °, π = 1.4761. IR f , i m : v m , = 3100, 1742, 1645, 1440, 1375, 1330, 1255, U 95, 1170, 1085, 1025, 990, 895 and 840 cm '. The compound has a floral, woody, ester-like odor.

Beispiel 3Example 3

In Analogie zu der in Beispiel 1 beschriebenen Weise wurden 18 g 2-(2-FormyIpropyl)-3-isopropenyl-l-methylcyclopent-l-en zu 2-(2-Carboxypropyl)-3-isopropenyl-1-methyl cyclopent-1-en (Ausbeute 13,2 g= 68%) oxydiert, Kp.ooo5 = 110°, IRri™: vmax = 3500-2500, 1705, 1642, 1460, 1440, 1418, 1375, 12S0, 1245, 940 und 895 cm-'. Die Verbindung hat einen schwach holzig säuerlichen Geruch-Beispiel 4In analogy to the manner described in Example 1, 18 g of 2- (2-formylpropyl) -3-isopropenyl-1-methylcyclopent-1-ene were converted into 2- (2-carboxypropyl) -3-isopropenyl-1-methylcyclopent-1 -en (yield 13.2 g = 68%) oxidized, b.p. ooo5 = 110 °, IRri ™: v max = 3500-2500, 1705, 1642, 1460, 1440, 1418, 1375, 12S0, 1245, 940 and 895 cm-'. The compound has a slightly woody, sour odor - Example 4

'n Analogie zu der in Beispiel 2 beschriebenen Weise wurden 3,12 g 2-(2-Carboxypropyl)-3-isopropenyl-lmethyl-cyclepent-l-en verestert. Das ölige Rohprodukt wurde an 100 g Kieselsäuregel mit Hexan/Äther (95 :1) chroniatographiert Nach Destillation im Hochvakuum wurden 2,96 g (87%) reines 2-(2-CarbomethoxypropyI)-3-isopropenyl-l-methyI-cyclopent-l-en erhalten;'n analogy to the manner described in Example 2 3.12 g of 2- (2-carboxypropyl) -3-isopropenyl-imethyl-cyclepent-1-ene were obtained esterified. The oily crude product was on 100 g silica gel with hexane / ether (95: 1) chroniatographed After distillation in a high vacuum, 2.96 g (87%) of pure 2- (2-carbomethoxypropylene) -3-isopropenyl-1-methyl-cyclopent-1-ene were obtained obtain;

Kp.0,02 = 70°, n? = 1,4728, IRnI1n: vmax = 3090, 1740, 1642,1460,1435,1370,1325,1285,1250,1 !95,1170,1120, 1085, 1060, 1035, 990, 890, 835 und 765 cm"'. Die Verbindung hat einen campherartigen Geruch.Kp 0.02 = 70 °, n? = 1.4728, IRnI 1n : v max = 3090, 1740, 1642, 1460, 1435, 1370, 1325, 1285, 1250.1! 95, 1170, 1120, 1085, 1060, 1035, 990, 890, 835 and 765 cm "'. The compound has a camphor-like odor.

Beispiel 5Example 5 GewichtsteileParts by weight 55 omposition mit phantasieblumiger Note:omposition with an imaginative floral note: 55 55 y-UndecaldCton, 1%*)y-UndecaldCton, 1% *) 2020th n-Nonylaldehyd, 1%*)n-nonylaldehyde, 1% *) 55 Laurinaldehyd, 10%*)Lauric aldehyde, 10% *) 100100 ω-n-Undecylenaldehyd, 10%*)ω-n-undecylenaldehyde, 10% *) 100100 4-Decen-l-al,10%*)4-decene-1-al, 10% *) 5050 Jasmin abs. synthetischJasmine abs. synthetic 3030th PhenyläthylalkoholPhenylethyl alcohol 55 Citronellol IaevoCitronellol Iaevo 1515th LinaloolLinalool 100100 FolrosiaGivaudanFolrosiaGivaudan 2525th StoraxölStorax oil 2525th 7-Hydroxy-3,7-dimethyloctan-l-a!7-Hydroxy-3,7-dimethyloctane-l-a! 5050 EugenolEugenol 5050 IsobutylsalicylatIsobutyl salicylate 6060 IsocamphylcyclohexanolIsocamphylcyclohexanol 1010 VetivenolVetivenol 2020th Ylang-YlangYlang-ylang 1515th Absolue MimosaAbsolute mimosa 1515th HeliotropinHeliotropin 2020th Civette natürlich entfettet, 10%*)Civette naturally defatted, 10% *) 100100 Äthylenbrassilat, 50%*)Ethylene brassilate, 50% *) 7070 Ambrette MoschusAmbrette musk BergamottölBergamot oil 100100 Absolue Flouveodorante,20%Absolute Flouveodorante, 20% 2-(2-Carbomethoxyäihyl)-3-isopro-2- (2-carbomethoxyethyl) -3-isopro- penyl-1 - methyl-cyclopent-1 -enpenyl-1-methyl-cyclopent-1-ene

10001000

·) In Phthalsäurediäthylester.·) In phthalic acid diethyl ester.

Claims (1)

Patentansprüche: 1. Cyclopenten-Verbindungen der FormelClaims: 1. Cyclopentene compounds of the formula R2 R 2 R1 R 1 (D(D worin R1 Hydroxy oder eine niedere Alkoxygruppe und R2 Wasserstoff, einen niederen Alkyl- oder niederen Alkylidenrest darstellen und die gestrichelt gezeichnete Linie eine fakultative Bindung bedeutet 2. Verfahren zur Herstellung von Cyclopentenen nach Anspruch 1, dadurch gekennzeichnet, daß man einen Aldehyd der Formelwherein R 1 is hydroxy or a lower alkoxy group and R 2 is hydrogen, a lower alkyl or lower alkylidene radical and the dashed line denotes an optional bond
DE19732365939 1972-03-17 1973-03-15 Cyclopentenes, processes for their production and fragrance compositions Expired DE2365939C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH404072A CH565728A5 (en) 1972-03-17 1972-03-17

Publications (3)

Publication Number Publication Date
DE2365939A1 DE2365939A1 (en) 1976-12-09
DE2365939B2 DE2365939B2 (en) 1980-05-08
DE2365939C3 true DE2365939C3 (en) 1981-01-15

Family

ID=4268690

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Application Number Title Priority Date Filing Date
DE19732365939 Expired DE2365939C3 (en) 1972-03-17 1973-03-15 Cyclopentenes, processes for their production and fragrance compositions
DE19732313017 Expired DE2313017C3 (en) 1972-03-17 1973-03-15 Cyclopentenes and processes for their preparation

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Application Number Title Priority Date Filing Date
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Country Status (6)

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JP (2) JPS5422968B2 (en)
CH (1) CH565728A5 (en)
DE (2) DE2365939C3 (en)
FR (1) FR2176786B1 (en)
GB (1) GB1379874A (en)
NL (2) NL160800C (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2513995C2 (en) * 1975-03-29 1984-04-12 Basf Ag, 6700 Ludwigshafen Cyclopentene derivatives
GB8813557D0 (en) * 1988-06-08 1988-07-13 James River Graphics Ltd Coating composition & coated paper
FR2735399B1 (en) * 1995-06-16 1997-07-25 Inst Francais Du Petrole NOVEL CATALYTIC COMPOSITION BASED ON TRANSITIONAL METAL COMPLEXES AND METHOD FOR THE HYDROGENATION OF UNSATURATED COMPOUNDS
US6187386B1 (en) * 1996-05-30 2001-02-13 Joseph W. Hundley Liquid sealant composition and method of using same

Also Published As

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JPS5422968B2 (en) 1979-08-10
DE2313017B2 (en) 1979-07-12
FR2176786A1 (en) 1973-11-02
NL7904191A (en) 1979-09-28
NL160800C (en) 1979-12-17
DE2365939A1 (en) 1976-12-09
DE2313017C3 (en) 1980-03-20
FR2176786B1 (en) 1979-01-12
JPS4911850A (en) 1974-02-01
NL7302559A (en) 1973-09-19
CH565728A5 (en) 1975-08-29
JPS5440616B2 (en) 1979-12-04
DE2365939B2 (en) 1980-05-08
DE2313017A1 (en) 1973-09-27
GB1379874A (en) 1975-01-08
JPS53109957A (en) 1978-09-26
NL160800B (en) 1979-07-16

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