FR2499069A1 - NEW 3-BENZYL-BUTANAL AND DERIVATIVES AND THEIR USE AS PERFUMES - Google Patents
NEW 3-BENZYL-BUTANAL AND DERIVATIVES AND THEIR USE AS PERFUMES Download PDFInfo
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- FR2499069A1 FR2499069A1 FR8201027A FR8201027A FR2499069A1 FR 2499069 A1 FR2499069 A1 FR 2499069A1 FR 8201027 A FR8201027 A FR 8201027A FR 8201027 A FR8201027 A FR 8201027A FR 2499069 A1 FR2499069 A1 FR 2499069A1
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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
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- 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
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- 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
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- 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
Abstract
Description
La psksente invention a pour objet un nouveau 3-benzyl- butanal et ses dérives d'hydrogénation répondant 9 la formule generale
dana laquelle
R1 est un groupe CH0 ou CH2OH, h est un groupe CH2 ou CH3 et la liaison en trait interrompu est une deuxième liaison facultative avec la condition supplémentaire que R2 est un groupe CH3 si R1 est un groupe CR2OR. The object of the present invention is a novel 3-benzylbutanal and its hydrogenation derivatives having the general formula
in which
R1 is CH0 or CH2OH, h is CH2 or CH3 and the dotted bond is a second optional bond with the additional proviso that R2 is CH3 if R1 is CR2OR.
Les nouveaux composes de l'invention sont donc le 2-methylène-3-benzy'-butanal (formule 1)
le 2-methyl-3-benzyl-butanal (formule 2)
et le 2-méthyl-3-benzyl-1-butanol (formule 3)
2-methyl-3-benzyl-butanal (formula 2)
and 2-methyl-3-benzyl-1-butanol (formula 3)
Ces composes ont des applications comme parfums. These compounds have applications as perfumes.
la préparation dee nouveaux composés s'effectue par hydroformylation du 2-methyl-3-phenyl-1-propène (formule 4) avec formation du 3-benzylbutanal formule 5) intermédiaire. La réaction ultérieure avec le formaldéhyde donne le composé 1. Les composés 2 e6 3 peuvent autre préparés à partir du composé 1 par hydrogénation. the preparation of the new compounds is carried out by hydroformylation of 2-methyl-3-phenyl-1-propene (formula 4) with formation of the intermediate 3-benzylbutanal formula 5). Subsequent reaction with formaldehyde gives compound 1. Compounds 2 and 6 can be prepared from compound 1 by hydrogenation.
Le schéma réactionnel suivant illustre la synthèse
Les conditions de réaction dans lesquelles s'effectue l'hydroformylation - donc la réaction du propène substitué avec l'hydrogène et le monoxyde de carbone - peuvent varier entre de larges limites. La température de réaction est en général comprise entre BO et 1500 c, elle est de préférence de 100 - 120 C la pression entre 150 et 300 bars, de préférence à 250 - 290 bars. On utilise comme catalyseur d'hydroformylation le cobalt, mais en particulier le rhodium. On ajoute les catalyseurs au méiane de réaction sous forme des métaux ou de composés métalliques. Il est particulièrement avantageux de choisir des composés qui sont solubles dans les milieux de réaction, comme par exemple les sels d'acide carboxyliques supé- rieurs.Selon un mode de mise en oeuvre préféré de 1thydroformylation, on opère en présence de composés qui forment des complexes avec les métaux-carbonyles se formant dans les conditions de réaction. Des composés complexants de ce type sont, par exemple, les triaLkyl- ou triarylphosphines. On les utilise avantageusement en excès, c'est- & dire en quantité qui dépasse celle nécessaire pour la formation du complexe. Il s'est révélé avantageux d'utiliser unexcès de 20 à 30 fois molaire. The reaction conditions in which hydroformylation takes place - hence the reaction of substituted propene with hydrogen and carbon monoxide - can vary within wide limits. The reaction temperature is in general between BO and 1500 c, it is preferably 100 - 120 C the pressure between 150 and 300 bar, preferably 250 - 290 bar. As the hydroformylation catalyst, cobalt, but especially rhodium, is used. The catalysts are added to the reaction mixture in the form of metals or metal compounds. It is particularly advantageous to choose compounds which are soluble in the reaction media, for example the higher carboxylic acid salts. According to a preferred embodiment of the hydroformylation, the reaction is carried out in the presence of compounds which form complexes with the metal carbonyls forming under the reaction conditions. Complexing compounds of this type are, for example, trialkyl- or triarylphosphines. They are advantageously used in excess, that is to say in an amount which exceeds that necessary for the formation of the complex. It has proved advantageous to use 20 to 30 times molar excess.
Le produit d'hydroformylation est isolé ou mélange réactionnel de manière connue, par exemple par distillation après séparation du catalyseur. Sans effectuer d'opérations de purification particulières, on fait ensuite réagir le 3-benzylbutanal avec le formaldéhyde ou une substance produisant du formaldéhyde comme, par exemple le paraformaldéhyde, en présence de quantités catalytiques d'une amine secondaire. Il se forme le 2-methylene-3-benzyl-butanal (formule 1). Le rapport molaire du catalyseur au 3-ben2ylbutanal est de 0,025 - 0,050 pour 1, on utilise de préférence la di-n-butylamine comme catalyseur, la réaction est effectuée sous pression normale a 90 - l000c. The hydroformylation product is isolated or reacted in known manner, for example by distillation after separation of the catalyst. Without performing particular purification operations, 3-benzylbutanal is then reacted with formaldehyde or a formaldehyde-producing substance such as, for example, paraformaldehyde, in the presence of catalytic amounts of a secondary amine. 2-Methylene-3-benzyl-butanal (Formula 1) is formed. The molar ratio of catalyst to 3-benzylbutanal is 0.025 to 0.050 to 1, di-n-butylamine is preferably used as a catalyst, the reaction is carried out under normal pressure at 90 to 1000 ° C.
L'hydrogénatlon du composé méthylé 1 s'effectue de manière connue par l'hydrogène en présence de catalyseurs appropriés. The hydrogenation of the methylated compound 1 is carried out in a known manner by hydrogen in the presence of suitable catalysts.
Selon les conditions d'hydrogénation, on obtient, soit l'aldéhyde saturé, le 2-méthyl-3-benzylbutanal (formule 2), soit l'alcool saturé, le 2-mdthyl-3-benzyl-l-butanol (formule 3).Depending on the hydrogenation conditions, either saturated aldehyde, 2-methyl-3-benzylbutanal (formula 2) or saturated alcohol, 2-methyl-3-benzyl-1-butanol (formula 3) are obtained. ).
Les catalyseurs aux métaux nobles, en particulier les catalyseurs au palladiuF sont appropries pour la préparation de l'aldéhyde saturé (formule 2). On les utilise sous forme de catalyseurs sur support, par exemple en quantités ds 0,1 a 2 % en poids, de prefé- rence d'environ 1 % en poids, par rapport 9 l'aldéhyde insaturé, avec le charbon actif ou l'oxyde d'aluminium comme support. La réaction se déroule des températures de 80 - 1300C, de préférence a 90 - 110 C et sous une pression d'hydrogène de 1 - 30 bars. The noble metal catalysts, in particular the palladiuF catalysts are suitable for the preparation of the saturated aldehyde (formula 2). They are used in the form of supported catalysts, for example in amounts of 0.1 to 2% by weight, preferably about 1% by weight, based on the unsaturated aldehyde, activated carbon or magnesium oxide. aluminum oxide as support. The reaction proceeds at temperatures of 80.degree. To 1300.degree. C., preferably at 90.degree.-110.degree. C. and at a hydrogen pressure of 1 to 30 bars.
Pour l'obtention de l'alcool saturé (formule 3), on hydrogène catalytiquement l'aldéhyde insaturé de manière également connue, l'hydrogène étant fixe selon une reaction å un ou deux stades. Dans l'hydrogénation en un stade, on fait réagir simultanément le groupe carbonyle et la double liaison avec l'hydrogène et on obtient directement l'alcool sature 9 partir de l'aldéhyde insaturé. Dans le cas de cette forme d'hydrogénation, on opère avantageusement en phase liquide en presence d'un agent diluant, par exemple le cyclohexane ou d'autres hydrocarbures ou en présence de monoalcools, par exemple 2-éthylhexanol, ou du produit final lui-meme. On utilise avantageusement comme catalyseurs des catalyseurs au nickel ayant une teneur en nickel de 20 à 100 % en poids, par rapport aux catalyseurs. On consi dere de préférence couve supports la terre d'infusoires ou l'oxyde d'aluminium. On opère habituellement dans un domaine de températures de 90 - 160 C et sous des pressions de 50 - 150 bars. Selon la teneur en nickel, on utilise 2 - 15 7. en poids de catalyseur, par rapport 9 l'aldéhyde insaturé
Dans le cas de l'hydrogénation en deux stades, après l'hydrogénation partielle en aldéhyde saturé decrite plus haut, on remplace le catalyseur au métal noble par un catalyseur au nickel.In order to obtain the saturated alcohol (formula 3), the unsaturated aldehyde is also catalytically hydrogenated in a known manner, the hydrogen being fixed in one or two stages. In the one-stage hydrogenation, the carbonyl group and the hydrogen double bond are simultaneously reacted and the saturated alcohol is obtained directly from the unsaturated aldehyde. In the case of this form of hydrogenation, the reaction is advantageously carried out in the liquid phase in the presence of a diluent, for example cyclohexane or other hydrocarbons or in the presence of monoalcohols, for example 2-ethylhexanol, or of the final product. -even. Nickel catalysts having a nickel content of from 20 to 100% by weight, based on the catalysts, are advantageously used as catalysts. The diatomaceous earth or aluminum oxide is preferably coated. The operation is usually carried out in a temperature range of 90.degree. To 160.degree. C. and at pressures of 50.degree. To 150.degree. Depending on the nickel content, 2 - 15% by weight of catalyst is used, relative to the unsaturated aldehyde.
In the case of the two-stage hydrogenation, after partial hydrogenation to the saturated aldehyde described above, the noble metal catalyst is replaced with a nickel catalyst.
Dans l'hydrogénation de l'aldéhyde saturé en alcool, la présence d'un solvant n'est pas nécessaire pour l'obtention d 'un bon résultat d'hydrogénation. Selon la teneur en nickel, on utilise 2 - 15 X en poids de catalyseur, par rapport a l'aldéhyde saturé. L'hydrogénation est effectuée, selon I'activité du catalyseur, à des températures de 90 - 1600C et sous une pression d'hydrogène de 50 - 150 bars.In the hydrogenation of aldehyde saturated with alcohol, the presence of a solvent is not necessary for obtaining a good hydrogenation result. Depending on the nickel content, 2 - 15% by weight of catalyst is used, relative to the saturated aldehyde. The hydrogenation is carried out, according to the activity of the catalyst, at temperatures of 90.degree.-160.degree. C. and under a hydrogen pressure of 50-150 bar.
La purification des produits d'hydrogénation s'effectue par distillation fractionnée. The purification of the hydrogenation products is carried out by fractional distillation.
Les nouveaux composés sont des liquides limpides d'odeur agréable ; on a rassemblé dans le tableau ci-dessous quelques propriétés physiques des composés de l'invention.
<tb><Tb>
<SEP> Point <SEP> Indice <SEP> de <SEP>
<tb> <SEP> d'ébullition <SEP> De"sit
<tb> <SEP> OC/7 <SEP> mbars <SEP> 20 <SEP> rSdraction
<tb> <SEP> C/7 <SEP> mbars <SEP>
<tb> <SEP> . <SEP> ~ <SEP>
<tb> 2-méthyldne-3- <SEP>
<tb> benzyl-butanal <SEP> 113 <SEP> 0,982 <SEP> 1,525
<tb> 2-mëthyl-3- <SEP>
<tb> benzyl-butanal <SEP> 123 <SEP> 0,967 <SEP> 1,508
<tb> 2-méthyl-3- <SEP>
<tb> benzyl-l-butanol <SEP> 128 <SEP> 0,969 <SEP> 1,516
<tb> <SEP> - <SEP> --------
Les composés selon l'invention trouvent des applications surtout comme parfums. Ils se caractérisent par des notes odorantes particulièrement intenses et persistantes de qualité et de plénitude odorantes élevées.<SEP> Point <SEP> Index <SEP> of <SEP>
<tb><SEP> Boiling <SEP> From "sit
<tb><SEP> OC / 7 <SEP> mbars <SEP> 20 <SEP> rSdraction
<tb><SEP> C / 7 <SEP> mbars <SEP>
<tb><SEP>.<SEP> ~ <SEP>
<tb> 2-methyldne-3- <SEP>
<tb> benzyl butanal <SEP> 113 <SEP> 0.982 <SEP> 1.525
<tb> 2-methyl-3- <SEP>
<tb> benzyl-butanal <SEP> 123 <SEP> 0.967 <SEP> 1.508
<tb> 2-methyl-3- <SEP>
<tb> benzyl-1-butanol <SEP> 128 <SEP> 0.969 <SEP> 1.516
<tb><SEP> - <SEP> --------
The compounds according to the invention find applications mainly as perfumes. They are characterized by particularly intense and persistent fragrant notes of high odor and high quality.
On a déja décrit dans la littérature quelques composés de structure semblable conne parfums. Ainsi, selon Arctander (Perfume and Flavor Chemicals, Nantclair 1969, Monographies 2172 et 2173), le 2-méthyl-4-phényl-butanal et le 3-méthyl-2-phényl-butanal possedent une odeur -fleurie, fruitée verte. Le 3-méthyl-4-phényl-valéralddhyde (Monographie 2204) a également une tendance parfumée dans la meme direction. Some compounds of similar structure with perfumes have already been described in the literature. Thus, according to Arctander (Perfume and Flavor Chemicals, Nantclair 1969, Monographs 2172 and 2173), 2-methyl-4-phenyl-butanal and 3-methyl-2-phenyl-butanal have a fruity, fruity-green odor. 3-methyl-4-phenyl-valeraldehyde (Monograph 2204) also has a scented tendency in the same direction.
Nais ces composés, en raison des procédés de prepa- ration coûteux, ne pouvaient pas trouver un domaine d'application important comme parfums. But these compounds, because of expensive preparation methods, could not find an important field of application as perfumes.
Les nouveaux composés ne présentent pas cette lacune. The new compounds do not present this gap.
Un autre avantage des nouveaux composés est leur bonne aptitudes se combiner en nouvelles nuances odorantes et leur particulière persistance. Another advantage of the new compounds is their good abilities to combine in new fragrant nuances and their particular persistence.
Les composés selon l'invention peuvent etre mélangés avec d'autres parfums dans les proportions les plus diverses pour donner des compositions odorantes. Mais, en général, la proportion des nouveaux parfums dans les compositions odorantes se situe entre 1 et 50 % en poids, par rapport b la composition totale. Ces compositions peuvent servir directement comme parfums, ou bien aussi parfumer des cosmétiques, tels que crèmes, lotions, eaux parfumées, aérosols, savons de toilette. The compounds according to the invention can be mixed with other fragrances in the most varied proportions to give fragrant compositions. In general, however, the proportion of new fragrances in the scented compositions is between 1 and 50% by weight, based on the total composition. These compositions can be used directly as perfumes, or also perfume cosmetics, such as creams, lotions, scented waters, aerosols, toilet soaps.
Les compositions peuvent aussi etre ajoutées à des produits techniques tels qu'agents de lavage et de nettoyage, agents désinfectants, agents de traitement des- textiles, etc., pour améliorer leur odeur. The compositions may also be added to technical products such as washing and cleaning agents, disinfectants, textile treatment agents, etc., to improve their odor.
Les exemples suivants illustrent l'invention sans toutefois en limiter la portée. The following examples illustrate the invention without, however, limiting its scope.
Exemple 1 2 methylène-3-benzyl-butanal
Dans un autoclave en acier, on effectue de manière connue l'hydroformyîation de 2000 g d'un mélange d'oléfines consistant en 90 2 % de 2-méthyl-3-phényl-l-propène et 9,8 Z de ss,ss-dimethylstyrène à une température de 100 C et sous une pression de 270 bars avec le rhodium & une concentration de 0,01 Z en poids (par rapport à l'olé- fine utilisée) corme catalyseur et la triphénylphosphine (rapport molaire : Rh : P=1 : 30) comme agent complexant.D'après l'analyse par chromatographie gazeuse, le melange de réaction débarrassé du catalyseur a la composition suivante
2-méthyl-3-phényl-1-propène 1,9 Z
ss,ss-diméthylstyrène 8,9 Z
3-méthyl-2-phényl-butanal 1,2 Z
3-benzyl-butanal 85,0 Z
autres composants 3,0 Z
A 1500 g de ce produit d'hydroformjlation dans un ballon à fond rond de 6 1, on ajoute 693 g de formaldéhyde en solution aqueuse à 37 Z et 47 g de di-n-butylamine et on chauffe au reflux pendant 2 heures. On traite par distillation fractionnée le produit de réaction brut consistant pour 85 Z en 2-méthylène-3-benzyl-butanal. Example 1 2 Methylene-3-benzyl-butanal
In a steel autoclave, hydroformylation of 2000 g of a mixture of olefins consisting of 90% 2-methyl-3-phenyl-1-propene and 9.8% ss, ss is carried out in a manner known per se. -dimethylstyrene at a temperature of 100 ° C. and at a pressure of 270 bar with rhodium at a concentration of 0.01% by weight (relative to the olefin used) as the catalyst and triphenylphosphine (molar ratio: Rh: P = 1: 30) as complexing agent. According to gas chromatographic analysis, the reaction mixture freed from the catalyst has the following composition
2-methyl-3-phenyl-1-propene 1.9 Z
ss, ss-dimethylstyrene 8.9 Z
3-methyl-2-phenyl-butanal 1.2 Z
3-benzyl-butanal 85.0 Z
other components 3.0 Z
To 1500 g of this hydroformylation product in a 6 1 round-bottomed flask is added 693 g of formaldehyde in 37% aqueous solution and 47 g of di-n-butylamine and refluxed for 2 hours. The crude reaction product consisting of 85% of 2-methylene-3-benzyl-butanal is treated by fractional distillation.
On obtient une fraction principale bouillant à 113 C/7 bars, avec 984 g de 2-mdthyldne-3-benzyl-butanal à 99,5 th (d20 = 0,982 nD20
4 = D=1 > 525
Exemple 2 2-méthyl-3-benzyl-butana
On hydrogène partiellement 500 g de 2-méthylène-3-benzylbutanal dans un autoclave en acier en présence de 5 g de catalyseur à 5 Z de palladium sur charbon actif sous 20 bars et à 100 C. Il se forme le 2-méthyl-3-benzyl-butanal (E 123 C/7mbars ; d20 = 0,967 ; n2D0 = 1,508), avec un rendement de 97 %.A main fraction boiling at 113 ° C./7 bar is obtained, with 984 g of 2-methylthien-3-benzyl-butanal at 99.5 th (d20 = 0.982 nD.sub.20).
4 = D = 1> 525
Example 2 2-methyl-3-benzyl-butana
500 g of 2-methylene-3-benzylbutanal are partially hydrogenated in a steel autoclave in the presence of 5 g of palladium-on-charcoal catalyst at 20 bar and at 100 ° C. 2-methyl-3 is formed. benzyl-butanal (E 123 C / 7mbars, d20 = 0.967, n2D0 = 1.508), with a yield of 97%.
Exemple 3 2=méthyl=3=benzyl-1-butanol
On mélange 500 g de 2-méthylène-3 -benzyl-butanal avec 500 E de cyclohexane et on hydrogène dans un autoclave en acier en présence d'un catalyseur au nickel sur support (environ 57 % en poids de Ni sur terre d'infusoires) à 1000C et sous 80 bars. On obtient le 2-méthyl-3-benzyl-l-butanol avec un rendement de 92 Z (E 128 C/7 abats 20 d 4 = ,969 ; n20 1 > 516). Example 3 2 = methyl = 3 = benzyl-1-butanol
500 g of 2-methylene-3-benzyl-butanal are mixed with 500 E of cyclohexane and hydrogenated in a steel autoclave in the presence of a supported nickel catalyst (approximately 57% by weight of Ni on infusorial earth ) at 1000C and under 80 bar. 2-Methyl-3-benzyl-1-butanol is obtained with a yield of 92% (E 128 C / 7 offal d 4 = 969, n 2 O 516).
I1 est entendu que l'invention n'est pas limitée aux modes de réalisation préférés décrits ci-dessus à titre d'illustration etque l'homme de l'art peut y apporter diverses modifications et divers changements sans toutefois s'écarter du cadre et de l'esprit de l'invention. It is to be understood that the invention is not limited to the preferred embodiments described above by way of illustration and that those skilled in the art may make various modifications and changes thereto without departing from the scope and of the spirit of the invention.
Claims (5)
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2499069A1 true FR2499069A1 (en) | 1982-08-06 |
| FR2499069B1 FR2499069B1 (en) | 1984-11-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8201027A Granted FR2499069A1 (en) | 1981-01-31 | 1982-01-22 | NEW 3-BENZYL-BUTANAL AND DERIVATIVES AND THEIR USE AS PERFUMES |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH647494A5 (en) |
| DE (1) | DE3103268C2 (en) |
| FR (1) | FR2499069A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0291849A2 (en) * | 1987-05-19 | 1988-11-23 | BASF Aktiengesellschaft | 4-Methyl-4-phenyl-pentan-1-als, their preparation and application as aroma chemicals |
Families Citing this family (5)
| 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 |
| 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 |
| 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 |
| JP6180115B2 (en) * | 2012-01-05 | 2017-08-16 | 花王株式会社 | Irritation mitigation agent |
Citations (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
Patent Citations (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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0291849A2 (en) * | 1987-05-19 | 1988-11-23 | BASF Aktiengesellschaft | 4-Methyl-4-phenyl-pentan-1-als, their preparation and application as aroma chemicals |
| EP0291849A3 (en) * | 1987-05-19 | 1989-03-15 | Basf Aktiengesellschaft | 4-methyl-4-phenyl-pentan-1-als, their preparation and application as aroma chemicals |
Also Published As
| Publication number | Publication date |
|---|---|
| CH647494A5 (en) | 1985-01-31 |
| FR2499069B1 (en) | 1984-11-23 |
| DE3103268A1 (en) | 1982-08-26 |
| DE3103268C2 (en) | 1985-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |