DE1643176A1 - Process for the production of compounds of the p-menthane series with fragrance properties - Google Patents

Process for the production of compounds of the p-menthane series with fragrance properties

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Publication number
DE1643176A1
DE1643176A1 DE19671643176 DE1643176A DE1643176A1 DE 1643176 A1 DE1643176 A1 DE 1643176A1 DE 19671643176 DE19671643176 DE 19671643176 DE 1643176 A DE1643176 A DE 1643176A DE 1643176 A1 DE1643176 A1 DE 1643176A1
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Prior art keywords
acyl
menthadiene
compounds
production
alkane
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DE19671643176
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German (de)
Inventor
Ernst Dipl-Chem Dr Alder
Guenther Dipl-Chem Dr Lucius
Manfred Prof Dipl- Muehlstaedt
Peter Dipl-Chem Richter
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CHEMISCHES KOM MILTITZ VEB
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CHEMISCHES KOM MILTITZ VEB
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Classifications

    • 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
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the rings

Description

Verfahren zur Herstellung von Verbindungen der p-menthanreihe mit riechstoffeigenschaften ble Erfindung betrifft ein Verfahren zur Herstellung von Heuartigen, bisher unbekannten Verbindungen aus 3-Acyl-#4-carenen, die suS?ezeichnete Riechstoffeigenschaft an besitzen. iXach dem DDR-Patent @r. 39 693 lassen sich aus dem in seliebigen @engen, z.B. aus deutschem Terpentinöl ge-@innbarem #3-Caren 3-Acyl-#4-carene herstellen. Process for the preparation of compounds of the p-menthan series with fragrance properties ble invention relates to a method for producing Hay-like, hitherto unknown compounds from 3-acyl- # 4-carenes, the sweet one Own fragrance property. iX according to the GDR patent @r. 39 693 can be omitted the # 3-carene, 3-acyl- # 4-carene, which can be obtained from German turpentine oil, for example produce.

@e die Gewinnung dieser 3-Acyl-#4-carene und deren Derivate in einen technisch einfach zu realisierenden Verfanren mit hohen ausbeuten leicht durchzuführen ist, leg der @rfindung die aufgabe zugrunde, weitere Varianten zu entwickeln, die unter Anwendung an sich bekannter Reaktionen (z.B. der Pyrolyse nach G. Ohloff, Ber. 93, 2673 (196G) und Tetrahedron Letters 42, 3795 (1965)) auf der Grundlage dieser Verbindungen zu Stoffen mit heuen R@echstoffeigenschaften führen.@e the production of these 3-acyl- # 4-carenes and their derivatives in one Technically easy to implement procedures with high yields are easy to carry out is, the @invention is based on the task of developing further variants that using reactions known per se (e.g. pyrolysis according to G. Ohloff, Ber. 93, 2673 (196G) and Tetrahedron Letters 42, 3795 (1965)) on the basis these compounds lead to substances with today's toxic properties.

Es wurde nun gefunden, da# sich die im DDR-Patent Nr.It has now been found that the GDR patent no.

39 693 beschriebenen 3-substituierten-#@-Carene unter Erhalt des Substituenten bei relativ niedrigen Temperaturen, vorzugsweise bei 350-600°C, unter Öffnung des Dreiringes zu 2-substituiert en-p-Menthadienen-5,8(9) in nohen Ausbeuten nach folgendem Formelschema pyrol-@ieren lassen: R = Acyl-, Alkan-(1'-01)- oder Alkan-(1'-acyloxy)-rest Dabei entstehen aus den 3-Acyl-#4-carenen (I) die 2-Acyl-p-menthadiene-5,8(9) (IV) und aus den 3-Alkan-(1'-01)-#4-carenen (II), die aus I leicht dargestellt werden können, die 2-Alkan-(1'-01)-p-menthadiene-5,8(9) (V). analog dazu entstehen aus den 3-Alkan-(1'-acyloxy)-#4-carenen (III) 2-Alkan-(1'-acyloxy)-p-menthadiene-5,8(9) (VI).39,693 described 3-substituted - # @ - carenes with retention of the substituent at relatively low temperatures, preferably at 350-600 ° C, with opening of the three-membered ring to 2-substituted en-p-menthadiene-5,8 (9) in close Pyrolytic yields according to the following equation: R = acyl, alkane (1'-01) or alkane (1'-acyloxy) radical. The 2-acyl-p-menthadienes-5 are formed from the 3-acyl- # 4-carenes (I) , 8 (9) (IV) and from the 3-alkane (1'-01) - # 4-carenes (II), which can easily be prepared from I, the 2-alkane (1'-01) - p-menthadiene-5.8 (9) (V). analogously, the 3-alkane (1'-acyloxy) - # 4-carenes (III) give 2-alkane (1'-acyloxy) -p-menthadienes-5,8 (9) (VI).

Der einheitliche stereospezifische Verlauf der Pyrolyse der angeführten 3-substituierten-#4-Carene und die Gewinnung von 2-substituierten-p-Menthadienen-5,8(9) in hohen Ausbeuten wird durch die 1,5-Wasserstofverschiebung an der Dinethylcyclopropylvinylgruppierung bedingt, da andererseits die analogen 3-substituierten-4 3-Carene bzw. Carane bei den angewandten Reaktionsbedingungen thermisch stabil waren und erst, wie gefunden wurde, bei wesentlich höheren Reaktionstemperaturen unter Dildung von kompliziert zusammengesetzten Kohlenwasserstoffgemischen---zerfallen. Die erfindungsgemäß hergestellten neuen 2-substituierten-p-Menthadiene-5,8(9) stellen ausgezeichnetze neue Riechstoffe mit starken, langhaftenden Geruchsnoten in Richtung holziffl, an den charakteristischen Geruch des Vetivers erinnernd, dar und eignen sich vorzüglich für den einsatz in Richstoffkompositionen.The uniform stereospecific course of the pyrolysis of the listed 3-substituted- # 4-carenes and the production of 2-substituted-p-menthadienes-5.8 (9) in high yields is due to the 1,5-hydrogen shift on the Dinethylcyclopropylvinylgruppierung conditional, since on the other hand the analogous 3-substituted-4 3-carenes or caranes the applied reaction conditions were thermally stable and only as found became complicated at much higher reaction temperatures with the formation of composite hydrocarbon mixtures --- disintegrate. The manufactured according to the invention new 2-substituted-p-menthadiene-5,8 (9) represent excellent new fragrances with strong, long-lasting odor notes in the direction of holziffl, on the characteristic ones Reminiscent of the smell of the vetiver, they are ideal for use in Rich compositions.

Darüber hinaus bilden sie Ausgangsprodukte für weitere Riechstoffsynthesen. Erfindungsgemäß lassen sich die 2-Acyl-p-menthadiene-5,8(9) (IV) leicht zu 2-Acyl-pcymolen (VII) dehydrieren. Die Hydrierung der 2-Acylp-menthadiene (IV) führt dagegen erfindungsgemäß mit Nickelkatalysatoren wahlweise zu 2-Acyl-p-menthanen (VIII) oder zu 2-Alkan-(i'-ol)-p-menthanen (IX).In addition, they form starting products for further odor synthesis. According to the invention, the 2-acyl-p-menthadienes-5,8 (9) (IV) can easily be converted into 2-acyl-pymols (VII) dehydrate. In contrast, the hydrogenation of the 2-acylp-menthadienes (IV) leads according to the invention with nickel catalysts optionally to 2-acyl-p-menthanes (VIII) or to 2-alkan (i'-ol) -p-menthanes (IX).

Letztere sind auch aus den 2-Alkanol-p-nuentlladienen 5,8(9) (V) durch katalytische Hydrierung erhältlich.The latter are also made from the 2-alkanol-p-nuentlladienes 5,8 (9) (V) catalytic hydrogenation available.

Die neuen homologen Terpenalkohole sind nach bekannten Methoden leicht zu den ungesättigten oder ges@ttigten bstern VI und X zu verestern. Auch diese Prodtikte können als wertvolle Riechstoffe Verwendung finden. The new homologous terpene alcohols can easily be esterified to the unsaturated or saturated bsters VI and X by known methods. These products can also be used as valuable fragrances.

R1 bzw. R2 = Alkylrest Beispiele 1. 2-Acetyl-p-menthadien-5,8(9) 1000 g 3-Acetyl-#4-caren wurden in einem 50 cm langen Kapillarrohr bei 540° pyrolysiert und das Pyrolyseprodukt wurde fraktioniert destilliert. R1 or R2 = alkyl radical Examples 1. 2-Acetyl-p-menthadiene-5.8 (9) 1000 g of 3-acetyl- # 4-carene were pyrolyzed at 540 ° in a 50 cm long capillary tube and the pyrolysis product was fractionally distilled.

Ausbeute: 80 % der Theorie, Sdp.10 112°, nD20 1,4885, d420 0,9470, [α]D20 + 373°. Yield: 80% of theory, boiling point 10 112 °, nD20 1.4885, d420 0.9470, [α] D20 + 373 °.

Ketongehalt: 10u y (Oximierung, ber. auf MG 178,3). Ketone content: 10u y (oximation, calculated on MW 178.3).

2. 2-Propionyl-p-menthadien-5,8(9) 100 gr 3-Propionyl-#4-caren wurden wie unter 1. beschieben umgesetzt und aufgearbeitet.2. 2-propionyl-p-menthadiene-5,8 (9) 100 grams of 3-propionyl- # 4-carene as described under 1. implemented and processed.

Ausbeute: 75 % der Theorie. Yield: 75% of theory.

Sdp.10 125°, nD20 1,4855.Bp 10 125 °, nD20 1.4855.

30 2-Butanoyl-p-menthadien-5, 8(9) 100 g 3-Butanoyl-#4-caren wurden wie unter 1. beschrieben umgesetzt und aufgearbeitet.30 2-butanoyl-p-menthadiene-5, 8 (9) 100 g of 3-butanoyl- # 4-carene implemented and worked up as described under 1..

Ausbeute: 70 % der Theorie. Yield: 70% of theory.

Sdp.10 138°, nD20 1,4878. Bp 10 138 °, nD 20 1.4878.

4. 2-Äthyl-(1'-01)-p-menthadien-5,8(9) 800 g 3-Äthyl-(1'-01)-#4-caren (Schmp. 84,5°) wurden wie unter 1. beschrieben bei 5300 pyrolysiert. Das Produkt wurde durch fraktionierte Destillation gereinigt.4. 2-Ethyl- (1'-01) -p-menthadiene-5.8 (9) 800 g of 3-ethyl- (1'-01) - # 4-carene (Melting point 84.5 °) were pyrolyzed as described under 1. at 5300. The product was purified by fractional distillation.

Ausbeute: 465 g eines zum Teil kristallisierten Produktes, das nach dem Umkristallisieren aus Cyclohexan bei 50-52° schmolz. Yield: 465 g of a partially crystallized product, which after the recrystallization from cyclohexane melted at 50-52 °.

[@]D20 + 14,5° (c=0,2 in Athanol). [@] 20 D + 14.5 ° (c = 0.2 in ethanol).

5. 2-Äthyl-(1'-acetoxy)-p-menthadien-5,8(9) a) 500 g 3-Äthyl-(1'-acetoxy)-#4-caren wurden im gleichen Kapillarrohr bei 5200 pyrolysiert und das Pyrolyseprodukt durch fraktionierte Destillation vom erhaltenen Vorlauf befreit.5. 2-Ethyl- (1'-acetoxy) -p-menthadiene-5,8 (9) a) 500 g of 3-ethyl- (1'-acetoxy) - # 4-carene were pyrolyzed in the same capillary tube at 5200 and the pyrolysis product through fractional distillation freed from the first runnings obtained.

Ausbeute: 60 % der Theorie. Yield: 60% of theory.

Sdp.10 1290, nD20 1,4751, d420 0,9608, [α]D20 + 308°, Estergehalt: 100 % (ber. auf MG 222,3). b) 100 g 2-kthy-(l'-ol)-p-enthadien-5,8(S) wurden mit 100 g Acetanhydrid und 10 g Natriumacetat nach üblicher Vorschrift umgesetzt und auf gearbeitet. Bp 10 1290, nD20 1.4751, d420 0.9608, [α] D20 + 308 °, ester content: 100% (calculated on MG 222.3). b) 100 g of 2-kthy- (l'-ol) -p-enthadiene-5,8 (S) were with 100 g of acetic anhydride and 10 g of sodium acetate are reacted according to the usual procedure and worked on.

Ausbeute: 90 % der Theorie. Yield: 90% of theory.

Sdp.10 1290, nD20 1,4744, d240 0,9601, [α]D20 +3110, Estergehalt: 100 % (ber. auf MG 222,3). Bp 10 1290, nD20 1.4744, d240 0.9601, [α] D20 +3110, ester content: 100% (calculated on MG 222.3).

6. 2-Acetyl-p-cymol 178 g 2-Acetyl-p-menthadien-5,8(9) wurden mit 64 g Schwefel auf 200° erhitzt. Das Rohprodukt wurde nach der Entschwefelung fraktioniert destilliert.6. 2-Acetyl-p-cymol 178 g of 2-acetyl-p-menthadiene-5,8 (9) were mixed with 64 g of sulfur heated to 200 °. The crude product was fractionated after desulfurization distilled.

Ausbeute: 45 % der theorie. Yield: 45% of theory.

Sdp.10 127°, nD20 1,5190, d420 0,977, [α]D20 # 0°, Ketongehalt: 98 % (Oximierung ber. auf MG 176,25). Bp 10 127 °, nD20 1.5190, d420 0.977, [α] D20 # 0 °, ketone content: 98% (oximation calculated on MW 176.25).

7. 2-Acetyl-p-menthan 100u g 2-Acetyl-p-menthadien-5m8 (9) wurden im Rührautoklaven bei 1000 mit 50 g Nickelkatalysator mit der für zwei Doppelbindungen berechneten Menge Wasserstoff hydriert. Nach der Destillation hatte das Produkt folgende Konstanten: Sdp.10 105°, nD20 1,4567, d420 0,8924, [α]D20 + 17,5°, Ketongehalt: 100 % (Oximierung ber, auf MG 182,3).7. 2-Acetyl-p-menthane 100u g of 2-acetyl-p-menthadiene-5m8 (9) were added in a stirred autoclave at 1000 with 50 g of nickel catalyst with the one for two double bonds calculated amount of hydrogen hydrogenated. After distillation the product had the following constants: Sdp.10 105 °, nD20 1.4567, d420 0.8924, [α] D20 + 17.5 °, Ketone content: 100% (oximation over, to MW 182.3).

Ausbeute: 80 % der Theorie. Yield: 80% of theory.

8. 2-Athyl-(1'-01)-p-menthan a) 100 g 2-Acetyl-p-menthadien-5,8(9) wurden bei 150°mit 5 g Nickelkatalysator im Schüttelautoklaven mit der für 2 Doppelbindungen und die Ketogruppe berechneten enge Wasserstoff hydriert Ausbeute: 95 g eines zum Teil kristallinen Produktes, das nach dem Umkristallisieren aus Cyclohexan bei 95,5° schmolz.8. 2-Ethyl- (1'-01) -p-menthane a) 100 g of 2-acetyl-p-menthadiene-5.8 (9) were at 150 ° with 5 g of nickel catalyst in a shaking autoclave with the one for 2 double bonds and the keto group calculated narrow hydrogen hydrogenated yield: 95 g of one for Part of crystalline product, which after recrystallization from cyclohexane at 95.5 ° melted.

[α]D20 - 2,5° (C = 0,1 inÄthanol). b) 100 g 2-Äthyl-(1'-01)-p-menthadien-5,8(9) (Schmp. 50-52°) wurden bei 900 mit 5 g Nickelkatalysator im Schüttelautoklaven mit der für zwei Doppelbindungen berechneten Menge Wasserstoff hydriert. Bs wurden 95 g Alkohol erhalten, der nach dem Umkristallisieren aus Cyclohexan bei 95,5, schmolz. [α]D20-2,5° (c = 0,1 in Äthanol). [α] 20 D - 2.5 ° (C = 0.1 in ethanol). b) 100 g of 2-ethyl- (1'-01) -p-menthadiene-5.8 (9) (Mp. 50-52 °) were at 900 with 5 g of nickel catalyst in a shaking autoclave the amount of hydrogen calculated for two double bonds. Bs became 95 g of alcohol obtained which, after recrystallization from cyclohexane, melted at 95.5. [α] D20-2.5 ° (c = 0.1 in ethanol).

9. 2-Äthyl-(1'-acetoxy)-p-menthan 100 g 2-Äthyl-(1'-01)-p-menthan wurden wie ühlich verestert und aufgearbeitet Ausbeute: 95 % der Theorie.9. 2-ethyl- (1'-acetoxy) -p-menthane 100 g of 2-ethyl- (1'-01) -p-menthane were esterified and worked up as usual. Yield: 95% of theory.

Sdp.10 124°, nD20 1,4551, d420 0,9322, [α]D20 + 10,2°, Estergehalt: 700 % (ber. auf MG 226,4). Bp 10 124 °, nD20 1.4551, d420 0.9322, [α] D20 + 10.2 °, ester content: 700% (calculated on MG 226.4).

Claims (5)

P a t e n t a n s p r ü c h e : 1. Verfahren zur Herstellung von 2-Acyl-, 2-Alkan-(i'-ol)- und 2-Alkan-(1'-acyloxy)-p-menthadienen-5,8(9), dadurch gekennzeichnet, daß man 3-Acyl-, 3-Alkan-(1'-01)- und 3-Alkan-(1'-acyloxy)-44-carene pyrolysiert. P a t e n t a n s p r ü c h e: 1. Process for the production of 2-acyl-, 2-alkan (i'-ol) - and 2-alkan (1'-acyloxy) -p-menthadiene-5,8 (9), thereby characterized in that 3-acyl-, 3-alkane (1'-01) - and 3-alkane (1'-acyloxy) -44-carenes pyrolyzed. 2. Verfahren nach Anspruch 1., dadurch gekennzeichnet, da# man vorzugsweise bei Temperaturen von 500-600° im Kapillarrohr pyrolysiert.2. The method according to claim 1, characterized in that # one is preferably Pyrolyzed at temperatures of 500-600 ° in the capillary tube. 3. Verfahren nach Anspruch 1. und 2., dadurch gekennzeichnet daß man die erhaltenen 2-Acyl-p-menthadiene-5,8(9) nach bekannten Verfahren zu 2-Acylp-cymolen dehydriert.3. The method according to claim 1 and 2, characterized in that one the 2-acyl-p-menthadiene-5,8 (9) obtained by known processes to give 2-acyl-p-cymolene dehydrated. 4. Verfahren nach Anspruch 1. und 2., dadurch gekennzeichnet, daß man die nach Anspruch 1. und 2. erhaltenen Verbindungen hydriert.4. The method according to claim 1 and 2, characterized in that the compounds obtained according to claims 1 and 2 are hydrogenated. 5. Verfahren nach Anspruch 1.> 2. und 4o, dadurch gekennzeichnet, daß man die nach Anspruch 10, und 4. erhaltenen homologen Terpenalkohole nach bekannten Verfahren verestert.5. The method according to claim 1.> 2. and 4o, characterized in that that the homologous terpene alcohols obtained according to claim 10 and 4 are known Esterified process.
DE19671643176 1967-02-16 1967-02-16 Process for the production of compounds of the p-menthane series with fragrance properties Pending DE1643176A1 (en)

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DEV0032981 1967-02-16

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997017314A1 (en) * 1995-11-10 1997-05-15 Henkel Kommanditgesellschaft Auf Aktien Carbonyl compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997017314A1 (en) * 1995-11-10 1997-05-15 Henkel Kommanditgesellschaft Auf Aktien Carbonyl compounds
US5932771A (en) * 1995-11-10 1999-08-03 Smithkline Beecham Corporation Carbonyl compounds

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