CH647494A5 - NEW FRAGRANCES. - Google Patents
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- CH647494A5 CH647494A5 CH46982A CH46982A CH647494A5 CH 647494 A5 CH647494 A5 CH 647494A5 CH 46982 A CH46982 A CH 46982A CH 46982 A CH46982 A CH 46982A CH 647494 A5 CH647494 A5 CH 647494A5
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- benzyl
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- butanal
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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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- 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
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- 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
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Gegenstand der vorliegenden Erfindung sind die im Patentanspruch 1 definierten Verbindungen: 2-Methylen-3-benzyl-butanal der Formel 1, 2-Methyl-3-benzyl-butanal der Formel 2, und 2-Methyl-3-benzyl-butanol der Formel 3. The present invention relates to the compounds defined in claim 1: 2-methylene-3-benzyl-butanal of the formula 1, 2-methyl-3-benzyl-butanal of the formula 2, and 2-methyl-3-benzyl-butanol of the formula 3rd
Weitere Gegenstände der Erfindung sind die in den Patentansprüchen 2-4 definierten Riechstoffe. Further objects of the invention are the fragrances defined in claims 2-4.
Die Herstellung der neuen Verbindungen erfolgt beispielsweise, wie im nachstehenden Reaktionsschema dargestellt, durch Hydroformylierung von 2-Methyl-3-phenyl-l-propen (Formel 4) unter Bildung des Zwischenproduktes 3-25 Benzylbutanal (Formel 5). Die weitere Umsetzung mit Formaldehyd liefert die Verbindung der Formel 1. Die Verbindungen der Formeln 2 und 3 sind aus der Verbindung der Formel 1 durch Hydrierung herstellbar. The new compounds are prepared, for example, as shown in the reaction scheme below, by hydroformylation of 2-methyl-3-phenyl-l-propene (formula 4) to form the intermediate 3-25 benzylbutanal (formula 5). Further reaction with formaldehyde gives the compound of formula 1. The compounds of formulas 2 and 3 can be prepared from the compound of formula 1 by hydrogenation.
Das folgende Reaktionsschema verdeutlicht die Synthe- The following reaction scheme illustrates the synthesis
30 se: 30 se:
c Ho c Ho
Die Reaktionsbedingungen unter denen die Hydroformylierung - also die Umsetzung des substituierten Propens mit Wasserstoff und Kohlenmonoxid - erfolgt, können in weiten Grenzen variiert werden. Die Reaktionstemperatur liegt im allgemeinen zwischen 80 und 150°C, bevorzugt bei 100-120 °C, der Druck zwischen 150 und 300 bar, bevorzugt bei 250-290 bar. Als Hydroformylierungskatalysator wird zweckmässig Kobalt, insbesondere aber Rhodium verwendet. Die Katalysatoren setzt man dem Reaktionsgemisch in Form der Metalle oder von Metallverbindungen zu. Besonders zweckmässig ist es solche Verbindungen auszuwählen, die im Reaktionsmedium löslich sind, wie z.B. die Salze höherer Carbonsäuren. Nach einer bevorzugten Ausführungsform der Hydroformylierung arbeitet man in Gegenwart von Verbindungen, die mit den unter den Reaktionsbedingungen entstehenden Metallcarbonylen Komplexverbindungen bilden. Komplexbildende Verbindungen solcher Art sind z. B. Trialkyl- oder Triarylphosphine. Zweckmässig setzt man sie im Überschuss ein, d.h. in einer solchen Menge, die diejenige übersteigt, die zur Bildung des Komplexes erforderlich ist. Bewährt hat sich die Anwendung eines 20- bis 30-fachen molaren Überschusses. The reaction conditions under which the hydroformylation - ie the reaction of the substituted propene with hydrogen and carbon monoxide - takes place can be varied within wide limits. The reaction temperature is generally between 80 and 150 ° C, preferably 100-120 ° C, the pressure between 150 and 300 bar, preferably 250-290 bar. Cobalt, but in particular rhodium, is expediently used as the hydroformylation catalyst. The catalysts are added to the reaction mixture in the form of the metals or metal compounds. It is particularly expedient to select those compounds which are soluble in the reaction medium, e.g. the salts of higher carboxylic acids. According to a preferred embodiment of the hydroformylation, the reaction is carried out in the presence of compounds which form complex compounds with the metal carbonyls formed under the reaction conditions. Complex-forming compounds of this type are e.g. B. trialkyl or triarylphosphines. It is expedient to use them in excess, i.e. in an amount exceeding that required to form the complex. The use of a 20 to 30-fold molar excess has proven successful.
Das Hydroformylierungsprodukt wird in bekannter Weise, z.B. durch Destillation nach Abtrennung des Katalysators, aus dem Reaktionsgemisch isoliert. Ohne besondere so Reinigungsoperationen durchzuführen, kann das 3-Ben-zylbutanal anschliessend mit Formaldehyd oder einer Formaldehyd bildenden Substanz, wie z.B. Paraformaldehyd, in Gegenwart katalytischer Mengen eines sekundären Amins umgesetzt werden. Es bildet sich 2-Methylen-3-benzyl-but-55 anal (Formel 1). Das Mol-Verhältnis von Katalysator zu 3-Benzylbutanal beträgt beispielsweise 0,025-0,050 zu 1, als Katalysator wird bevorzugt Di-n-butylamin verwendet, die Reaktion wird zweckmässig bei 90-100 °C unter Normaldruck ausgeführt. The hydroformylation product is used in a known manner, e.g. by distillation after removal of the catalyst, isolated from the reaction mixture. Without performing cleaning operations in this way, the 3-benzylbutanal can subsequently be treated with formaldehyde or a formaldehyde-forming substance such as e.g. Paraformaldehyde, are reacted in the presence of catalytic amounts of a secondary amine. It forms 2-methylene-3-benzyl-but-55 anal (Formula 1). The molar ratio of catalyst to 3-benzylbutanal is, for example, 0.025-0.050 to 1, di-n-butylamine is preferably used as the catalyst, the reaction is conveniently carried out at 90-100 ° C. under normal pressure.
60 Die Hydrierung der Methylverbindung 1 erfolgt in bekannter Weise in Gegenwart geeigneter Katalysatoren mittels Wasserstoff. In Abhängigkeit von den Hydrierbedingungen erhält man entweder den gesättigten Aldehyd 2-Methyl-3-benzylbutanal (Formel 2) oder den gesättigten Alkohol 2-65 Methyl-3-benzyl-l-butanol (Formel 3). 60 The hydrogenation of methyl compound 1 is carried out in a known manner in the presence of suitable catalysts using hydrogen. Depending on the hydrogenation conditions, either the saturated aldehyde 2-methyl-3-benzylbutanal (formula 2) or the saturated alcohol 2-65 methyl-3-benzyl-1-butanol (formula 3) is obtained.
Für die Herstellung des gesättigten Aldehyds (Formel 2) sind Edelmetallkatalysatoren, insbesondere Palladiumkatalysatoren, geeignet. Sie werden als Trägerkatalysatoren, z.B. Precious metal catalysts, in particular palladium catalysts, are suitable for the preparation of the saturated aldehyde (formula 2). They are used as supported catalysts, e.g.
3 3rd
647 494 647 494
mit Aktivkohle oder Aluminiumoxid als Träger in Mengen von 0,1 bis 2 Gew.-%, vorzugsweise etwa 1 Gew.-%, bezogen auf den ungesättigten Aldehyd, eingesetzt. Die Reaktion verläuft bei Temperaturen von 80-130 °C, vorzugsweise 90-110 °C, und einem Wasserstoffdruck von 1-30 bar. with activated carbon or aluminum oxide as a carrier in amounts of 0.1 to 2 wt .-%, preferably about 1 wt .-%, based on the unsaturated aldehyde. The reaction takes place at temperatures of 80-130 ° C, preferably 90-110 ° C, and a hydrogen pressure of 1-30 bar.
Zur Gewinnung des gesättigten Alkohols (Formel 3) For the production of saturated alcohol (Formula 3)
wird der ungesättigte Aldehyd ebenfalls in bekannter Weise kataly tisch hydriert, wobei der Wasserstoff in ein- oder zweistufiger Reaktion angelagert wird. Bei einstufiger Hydrierung setzt man gleichzeitig Carbonylgruppe und Doppelbindung mit Wasserstoff um und erhält unmittelbar aus dem ungesättigten Aldehyd den gesättigten Alkohol. Zweckmässig arbeitet man bei dieser Form der Hydrierung in flüssiger Phase in Gegenwart eines Verdünnungsmittels, z.B. Cyclo-hexan oder andere Kohlenwasserstoffe oder in Gegenwart von einwertigen Alkoholen, z. B. 2-Ethylhexanol oder dem Endprodukt selbst. Als Katalysatoren verwendet man zweckmässigerweise Nickelkatalysatoren mit einem Gehalt von 20 bis 100 Gew.-% Nickel, bezogen auf den Katalysator. Als Träger kommen bevorzugt Kieselgur oder Aluminiumoxid in Betracht. Üblicherweise arbeitet man in einem Temperaturbereich von 90-160 °C und bei Drucken von 50-150 bar. Je nach dem Nickelgehalt setzt man 2-15 Gew.-% Katalysator, bezogen auf den ungesättigten Aldehyd, ein. the unsaturated aldehyde is also catalytically hydrogenated in a known manner, the hydrogen being added in a one- or two-stage reaction. In a single-stage hydrogenation, the carbonyl group and double bond are reacted with hydrogen at the same time and the saturated alcohol is obtained directly from the unsaturated aldehyde. This form of hydrogenation is advantageously carried out in the liquid phase in the presence of a diluent, e.g. Cyclo-hexane or other hydrocarbons or in the presence of monohydric alcohols, e.g. B. 2-ethylhexanol or the end product itself. The catalysts used are advantageously nickel catalysts with a content of 20 to 100% by weight of nickel, based on the catalyst. Diatomaceous earth or aluminum oxide are preferred carriers. Usually one works in a temperature range of 90-160 ° C and at pressures of 50-150 bar. Depending on the nickel content, 2-15% by weight of catalyst, based on the unsaturated aldehyde, is used.
Bei zweistufiger Hydrierung wird nach der oben beschriebenen partiellen Hydrierung zum gesättigten Aldehyd der Edelmetallkatalysator gegen einen Nickelkatalysator ausgetauscht. Bei der Hydrierung des gesättigten Aldehyds zum gesättigten Alkohol ist zur Erreichung eines guten Hydrierergebnisses die Gegenwart eines Lösungsmittels nicht erforderlich. Je nach Nickelgehalt setzt man 2-15 Gew.-% Katalysator, bezogen auf den gesättigten Aldehyd, ein. Die Hydrierung wird in Abhängigkeit von der Aktivität des Katalysators, zweckmässig bei Temperaturen von 90-160 °C und einem Wasserstoffdruck von 50-150 bar vorgenommen. In the case of two-stage hydrogenation, the noble metal catalyst is replaced by a nickel catalyst after the partial hydrogenation to saturated aldehyde described above. When hydrogenating the saturated aldehyde to the saturated alcohol, the presence of a solvent is not necessary to achieve a good hydrogenation result. Depending on the nickel content, 2-15% by weight of catalyst, based on the saturated aldehyde, is used. Depending on the activity of the catalyst, the hydrogenation is expediently carried out at temperatures of 90-160 ° C. and a hydrogen pressure of 50-150 bar.
Die Reinigung der Hydrierungsprodukte kann durch fraktionierte Destillation erfolgen. The hydrogenation products can be purified by fractional distillation.
Die neuen Verbindungen sind wasserklare Flüssigkeiten von angenehmem Geruch; einige physikalische Eigenschaften sind in der nachfolgenden Tabelle zusammengestellt. The new compounds are water-clear liquids with a pleasant smell; some physical properties are summarized in the table below.
Siedepunkt Dichte Brechnungsindex "C/7 mbar d2° nf)° Boiling point density refractive index "C / 7 mbar d2 ° nf) °
2-MethyIen-3-benzyl- 2-methylene-3-benzyl
butanal butanal
113 113
0,982 0.982
1,525 1.525
2-Methyl-3- 2-methyl-3-
benzyl-butanal benzyl butanal
123 123
0,967 0.967
1,508 1.508
2-Methyl-3- 2-methyl-3-
benzyl-l-butanol benzyl-l-butanol
128 128
0,969 0.969
1,516 1,516
Die erfindungsgemässen Verbindungen finden vor allem als Riechstoffe Anwendung. Sie zeichnen sich durch besonders intensive und nachhaltige Geruchsnoten von hoher Geruchsqualität und Geruchsfülle aus. The compounds according to the invention are used primarily as fragrances. They are characterized by particularly intense and sustainable odor notes of high odor quality and rich odor.
In der Literatur sind bereits einige Verbindungen ähnlicher Struktur als Riechstoffe beschrieben worden. So besitzen nach Arctander («Perfume and Flavor Chemicals», Montclair 1969, Monographie 2172 und 2173) 2-Methyl-4-phenyl-butanal und 3-Methyl-2-phenyl-butanal einen blumigen, grün-fruchtigen Geruch. In die gleiche Geruchsrichtung tendiert auch der 3-Methyl-4-phenyI-valeraldehyd (Monographie 2204). Some compounds with a similar structure have already been described as fragrances in the literature. According to Arctander ("Perfume and Flavor Chemicals", Montclair 1969, monograph 2172 and 2173), 2-methyl-4-phenyl-butanal and 3-methyl-2-phenyl-butanal have a floral, green-fruity smell. 3-Methyl-4-phenyI-valeraldehyde (monograph 2204) also tends to smell the same way.
Aufgrund der aufwendigen Herstellverfahren konnten diese Verbindungen als Riechstoffe jedoch keinen grossen Anwendungsbereich finden. However, due to the complex manufacturing processes, these compounds could not find a wide range of uses as fragrances.
Die neuen Verbindungen weisen diesen Mangel nicht auf. The new connections do not have this defect.
Ein weiterer Vorteil der neuen Stoffe ist ihre gute Kombinationsfähigkeit zu neuartigen Geruchsnuancen und ihre besondere Haftfestigkeit. Another advantage of the new fabrics is their good ability to combine with new types of smell and their special adhesive strength.
Die erfindungsgemässen Verbindungen können mit anderen Riechstoffen in verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen gemischt werden. Im allgemeinen wird sich jedoch der Anteil der neuen Riechstoffe in den Riechstoffkompositionen in den Mengen von 1 bis 50 Gew.-%, bezogen auf die gesamte Komposition, bewegen. Derartige Kompositionen können direkt als Parfume oder auch zur Parfumierung von Kosmetika, wie Cremen, Lotionen, Duftwässern, Aerosolen, Toilettenseifen, dienen. The compounds according to the invention can be mixed with other fragrances in a wide variety of proportions to give new fragrance compositions. In general, however, the proportion of new fragrances in the fragrance compositions will range from 1 to 50% by weight, based on the overall composition. Such compositions can be used directly as perfumes or for perfuming cosmetics such as creams, lotions, fragrant waters, aerosols, toilet soaps.
Die Kompositionen können auch zur Geruchsverbesserung technischen Produkten wie Wasch- und Reinigungsmittel, Desinfektionsmittel, Textilbehandlungsmittel usw., beigesetzt werden. The compositions can also be used to improve the smell of technical products such as washing and cleaning agents, disinfectants, textile treatment agents, etc.
Im folgenden wird die Herstellung der neuen Verbindungen beschrieben: (%- und ppm-Angaben sind gewichtsmäs-sig). The preparation of the new compounds is described below: (% and ppm data are by weight).
Beispiel 1 2-Methylen-3-benzyl-butanal Example 1 2-methylene-3-benzyl-butanal
In einem Stahlautoklaven werden 2000 g eines Olefinge-misches, bestehend aus 90,2% 2-Methyl-3-phenyl-l-propen und 9,8% ß,ß-Dimethylst} rol in bekannter Weise bei einer Temperatur von 100 °C und einem Druck von 270 bar hy-droformyliert, Katalysator ist Rhodium in einer Konzentration von 100 ppm, (bezogen auf eingesetztes Olefin) und Tri-phenylphosphin (Molverhältnis Rh: P = 1:30) als Komp.lex-bildner. Das vom Katalysator befreite Reaktionsgemisch hat nach gaschromatographischer Analyse folgende Zusammensetzung: In a steel autoclave, 2000 g of an olefin mixture consisting of 90.2% 2-methyl-3-phenyl-l-propene and 9.8% ß, ß-dimethylst} stol are known in a known manner at a temperature of 100 ° C. and a pressure of 270 bar hydrodylated, the catalyst is rhodium in a concentration of 100 ppm (based on the olefin used) and tri-phenylphosphine (molar ratio Rh: P = 1:30) as complex complexing agent. The reaction mixture freed from the catalyst has the following composition according to gas chromatographic analysis:
2-Methyl-3-phenyl-1 -propen 1,9% ß,ß-Dimethylstyrol 8,9% 2-methyl-3-phenyl-1-propene 1.9% ß, ß-dimethylstyrene 8.9%
3-Methyl-2-phenyl-butanal 1,2% 3-Benzyl-butanal 85,0% Sonstige Komponenten 3,0% 3-methyl-2-phenyl-butanal 1.2% 3-benzyl-butanal 85.0% other components 3.0%
1500 g dieses Hydroformylierungsproduktes werden in einem 61-Rundkolben mit 693 g 37%igem Formalin und 47 g Di-n-butylamin versetzt und zwei Stunden lang unter Rückfluss erwärmt. Das zu 85% aus 2-Methylen-3-benzyl-butanal bestehende rohe Reaktionsprodukt wird durch fraktionierte Destillation aufgearbeitet. Man erhält eine bei 113 °C/7 mbar siedende Hauptfraktion, mit 984 g 99,5%igem 2-Methylen-3-benzyl-butanal (d420 0,982; nD20 1,525). 1500 g of this hydroformylation product are mixed in a 61-round flask with 693 g of 37% formalin and 47 g of di-n-butylamine and heated under reflux for two hours. The crude reaction product, consisting of 2% methylene-3-benzyl-butanal, is worked up by fractional distillation. A main fraction boiling at 113 ° C./7 mbar is obtained, with 984 g of 99.5% 2-methylene-3-benzyl-butanal (d420 0.982; nD20 1.525).
Beispiel 2 2-Methyl-3-benzyl-butanal 500 g 2-Methylen-3-benzyl-butanal werden in einem Stahlautoklaven in Gegenwart von 5 g 5%igem Pd/Aktivkohle-Katalysator bei 20 bar und 100 °C partiell hydriert. Es entsteht in 97%iger Ausbeute 2-Methyl-3-benzyl-butanal (Kp 123 °C/7 mbar; d420 0,967; nD20 1,508). Example 2 2-methyl-3-benzyl-butanal 500 g of 2-methylene-3-benzyl-butanal are partially hydrogenated in a steel autoclave in the presence of 5 g of 5% Pd / activated carbon catalyst at 20 bar and 100 ° C. It produces 97% yield of 2-methyl-3-benzyl-butanal (bp 123 ° C / 7 mbar; d420 0.967; nD20 1.508).
Beispiel 3 2-Methyl-3 -benzyl-1 -butanol 500 g 2-Methylen-3-benzyl-butanal werden mit 500 g Cyclohexan gemischt und in einem Stahlautoklaven in Gegenwart eines Nickel-Trägerkatalysators (etwa 57 Gew.-% Ni auf Kieselgur) bei 100°C.und 80 bar hydriert. 2-Methyl-3-benzyl-l-butanol wird in 92%iger Ausbeute erhalten (Kp 128/7 mbar; d420 0,969; nD201,516). Example 3 2-methyl-3-benzyl-1-butanol 500 g of 2-methylene-3-benzyl-butanal are mixed with 500 g of cyclohexane and in a steel autoclave in the presence of a supported nickel catalyst (about 57% by weight of Ni on diatomaceous earth ) hydrogenated at 100 ° C and 80 bar. 2-Methyl-3-benzyl-l-butanol is obtained in 92% yield (bp 128/7 mbar; d420 0.969; nD201.516).
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Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813103268 DE3103268C2 (en) | 1981-01-31 | 1981-01-31 | 2-methylen-3-benzyl-butanal, 2-methyl-3-benzyl-butanal, 2-methyl-3-benzyl-butanol and their use as odoriferous substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH647494A5 true CH647494A5 (en) | 1985-01-31 |
Family
ID=6123726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH46982A CH647494A5 (en) | 1981-01-31 | 1982-01-26 | NEW FRAGRANCES. |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH647494A5 (en) |
| DE (1) | DE3103268C2 (en) |
| FR (1) | FR2499069A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3439203A1 (en) * | 1984-10-26 | 1986-04-30 | Basf Ag, 6700 Ludwigshafen | 1-PHENYL-2-METHYL-3-HYDROXY- (3-ALKOXY) -ALKYL COMPOUNDS, THE PRODUCTION AND USE THEREOF AS A FRAGRANT |
| US4650898A (en) * | 1984-12-14 | 1987-03-17 | International Flavors & Fragrances Inc. | Uses of methyl phenyl pentanol derivatives in augmenting or enhancing the aroma or taste of consumable materials |
| US4610812A (en) * | 1984-12-14 | 1986-09-09 | International Flavors & Fragrances Inc. | Uses of methyl phenyl pentanol derivatives in augmenting or enhancing the aroma or taste of consumable materials |
| US4632831A (en) * | 1984-12-14 | 1986-12-30 | International Flavors & Fragrances Inc. | Uses of methyl phenyl pentanol derivatives in augmenting or enhancing the aroma or taste of consumable materials |
| DE3716730A1 (en) * | 1987-05-19 | 1988-12-01 | Basf Ag | 4-METHYL-4-PHENYL-1-PENTANALE, THE PRODUCTION AND USE THEREOF AS A FRAGRANT |
| JP6180115B2 (en) * | 2012-01-05 | 2017-08-16 | 花王株式会社 | Irritation mitigation agent |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7502553A (en) * | 1975-02-13 | 1976-08-17 | Ruhrchemie Ag | Hydroformylated tert. butyl- and isopropyl allyl benzenes - useful aromatizing cpds |
| US4217253A (en) * | 1978-10-06 | 1980-08-12 | International Flavors & Fragrances Inc. | Mixture of 3-methyl-1-phenyl-pentanol-5 or its isomers and butanoyl cyclohexane derivatives |
-
1981
- 1981-01-31 DE DE19813103268 patent/DE3103268C2/en not_active Expired
-
1982
- 1982-01-22 FR FR8201027A patent/FR2499069A1/en active Granted
- 1982-01-26 CH CH46982A patent/CH647494A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3103268A1 (en) | 1982-08-26 |
| DE3103268C2 (en) | 1985-04-11 |
| FR2499069B1 (en) | 1984-11-23 |
| FR2499069A1 (en) | 1982-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |