CH479515A - Process for the preparation of unsaturated aldehydes - Google Patents

Process for the preparation of unsaturated aldehydes

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Publication number
CH479515A
CH479515A CH1365267A CH1365267A CH479515A CH 479515 A CH479515 A CH 479515A CH 1365267 A CH1365267 A CH 1365267A CH 1365267 A CH1365267 A CH 1365267A CH 479515 A CH479515 A CH 479515A
Authority
CH
Switzerland
Prior art keywords
sub
aromatic
substituted
heterocyclic
groups
Prior art date
Application number
CH1365267A
Other languages
French (fr)
Inventor
Francis Dr Thomas Alan
Original Assignee
Firmenich & Cie
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
Priority claimed from CH751167A external-priority patent/CH473753A/en
Application filed by Firmenich & Cie filed Critical Firmenich & Cie
Priority to CH1365267A priority Critical patent/CH479515A/en
Priority to CH697268A priority patent/CH510602A/en
Priority to US731277A priority patent/US3654309A/en
Priority to GB1233221D priority patent/GB1233221A/en
Priority to GB1233222D priority patent/GB1233222A/en
Priority to NL6807345A priority patent/NL6807345A/xx
Priority to DE19681768552 priority patent/DE1768552A1/en
Priority to FR1582515D priority patent/FR1582515A/fr
Publication of CH479515A publication Critical patent/CH479515A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/201—Compounds of unspecified constitution characterised by the chemical reaction for their preparation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
    • 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
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO 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
    • C07C45/513—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms

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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)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  



  Procédé pour la préparation d'aldéhydes non saturés
 La présente invention a pour objet un procédé de préparation d'aldéhydes non saturés de formule I suivante :
EMI1.1     

 Dans les formules   I,    II et III, les groupes R,   R. i, Rg,      RS,      R4,      RÏs RGF R7 et R8 représentent l'hydrogène    ou des restes aromatiques, hétérocycliques ou aliphatiques linéaires ou ramifiés, libres ou reliés entre eux de façon à former des cycles, saturés ou non saturés, substitués ou non par des restes aromatiques ou hétérocycliques, tandis que R'représente un reste aliphatique,   alicycli-    que, aromatique ou hétérocyclique pouvant tre aisément scindé, par exemple méthyle, benzyle, phényle ou furanyle.

   Il est à noter que   R',    étant éliminé lors de la   réac-    tion, n'a pas d'influence sur la structure du produit final et l'importance de sa nature est d'ordre secondaire.



   Conformément à un mode d'exécution du procédé de l'invention on chauffe, en présence d'un catalyseur comportant au moins 7 atomes de carbone et de   préfé-    rence, au plus 25 atomes de carbone.



   Certains de ces aldéhydes peuvent tre utilisés avan  tageusement    dans des compositions de parfums ou d'arômes.



   Le procédé, objet de l'invention, consiste à condenser, en présence d'un catalyseur de cyclisation, un éther vinylique répondant à la formule générale II avec un alcool allylique répondant à la formule III :
EMI1.2     
 de condensation, l'alcool allylique substitué III avec l'éther vinylique substitué   II,    à des températures comprises entre 40 et 160  mais de préférence au voisinage de 100  pendant une période dépendant de la réactivité des matières de départ, laquelle est généralement liée à la nature des substituants R à   R8    selon le mode approximatif suivant :

   la réactivité est généralement en raison directe du pouvoir électronique répulsif des groupes RI,   R3    et R4 et du pouvoir électronique attracteur des groupes   Ro, RY, RS, ces    pouvoirs étant évalués selon les règles usuelles.



   Comme catalyseur, on peut utiliser des sels de métaux ayant la propriété de former des complexes d'addition avec les oléfines tels, par exemple, de métaux appartenant à la   4e,    5e ou 6e période des éléments, comme le cobalt, l'argent ou le mercure.



   Suivant un mode d'exécution du procédé de   l'inven-      tion,    on chauffe en présence d'acétate mercurique, par exemple   l'éther 2-méthylbutadiényl éthylique    (II, R,   = CH"Rz = Ro = R4 = H et R = GH-,) avec, comme    alcool allylique III, l'alcool   crotylique    (III, R = R5 =   RG      = R ; = H, R = CH3).    On obtient dans ce cas le   2-mé-      thyloctadien- (2, 6)-al- (1). Il    va de soi que cet exemple n'est nullement limitatif et que d'autres éthers   butadié-    niques et d'autres alcools allyliques se prtent également au procédé suivant l'invention.



   L'exemple qui suit illustre la mise en oeuvre de l'invention.



  Exemple :
 Préparation du   2-méthyloctadien- (2, 6)-al- (I)   
 Sous protection   d'azote,    on chauffe   17 h à 100     un mélange d'alcool   crotylique    (20   g),    d'éther 2-méthylbuta  diényl    éthylique   (50g), d'acétate    mercurique (6,6g) et d'acétate de sodium (2,7g). Après refroidissement on ajoute du carbonate de potassium anhydre   (5g),    agite vigoureusement et filtre. On distille le filtrat et recueille la fraction passant à   78-80 /10    Torr. On obtient ainsi un rendement de   40 ouzo    de   2-méthyloctadien-(2, 6)-al-(1)    presque pur selon l'analyse par chromatographie en phase gazeuse.

   Par les méthodes habituelles on prépare facilement les dérivés   suivants : dinitrophénylhydrazone,   
F.   139-1400,    semicarbazone, F.   153-1550.   




  



  Process for the preparation of unsaturated aldehydes
 The present invention relates to a process for the preparation of unsaturated aldehydes of the following formula I:
EMI1.1

 In formulas I, II and III, the groups R, R. i, Rg, RS, R4, R Rs RGF R7 and R8 represent hydrogen or linear or branched aromatic, heterocyclic or aliphatic residues, free or linked to one another. so as to form rings, saturated or unsaturated, substituted or not by aromatic or heterocyclic residues, while R ′ represents an aliphatic, alicyclic, aromatic or heterocyclic residue which can be easily split, for example methyl, benzyl, phenyl or furanyl.

   It should be noted that R ', being eliminated during the reaction, has no influence on the structure of the final product and the importance of its nature is of secondary order.



   In accordance with one embodiment of the process of the invention, heating is carried out in the presence of a catalyst comprising at least 7 carbon atoms and preferably at most 25 carbon atoms.



   Some of these aldehydes can be used advantageously in perfume or flavoring compositions.



   The process which is the subject of the invention consists in condensing, in the presence of a cyclization catalyst, a vinyl ether corresponding to general formula II with an allyl alcohol corresponding to formula III:
EMI1.2
 condensation, substituted allylic alcohol III with substituted vinyl ether II, at temperatures between 40 and 160 but preferably in the region of 100 for a period depending on the reactivity of the starting materials, which is generally related to the nature of the substituents R to R8 according to the following approximate mode:

   the reactivity is generally a direct ratio of the repulsive electronic power of the RI, R3 and R4 groups and of the attracting electronic power of the Ro, RY, RS groups, these powers being evaluated according to the usual rules.



   As catalyst, it is possible to use salts of metals having the property of forming addition complexes with olefins such, for example, of metals belonging to the 4th, 5th or 6th period of the elements, such as cobalt, silver or Mercury.



   According to one embodiment of the process of the invention, heating is carried out in the presence of mercuric acetate, for example 2-methylbutadienyl ethyl ether (II, R, = CH "Rz = Ro = R4 = H and R = GH-,) with, as allyl alcohol III, crotyl alcohol (III, R = R5 = RG = R; = H, R = CH3). In this case, 2-methyloctadien- (2, 6) -al- (1) It goes without saying that this example is in no way limiting and that other butadiene ethers and other allyl alcohols are also suitable for the process according to the invention.



   The example which follows illustrates the implementation of the invention.



  Example:
 Preparation of 2-methyloctadien- (2, 6) -al- (I)
 Under nitrogen protection, a mixture of crotyl alcohol (20 g), 2-methylbuta dienyl ethyl ether (50g), mercuric acetate (6.6g) and sodium acetate is heated for 17 h at 100 (2.7g). After cooling, anhydrous potassium carbonate (5g) is added, stirred vigorously and filtered. The filtrate is distilled off and the fraction passing through 78-80 / 10 Torr is collected. There is thus obtained a yield of 40 ouzo of 2-methyloctadien- (2, 6) -al- (1) which is almost pure according to the analysis by gas chromatography.

   By the usual methods, the following derivatives are easily prepared: dinitrophenylhydrazone,
F. 139-1400, semicarbazone, F. 153-1550.

Claims (1)

REVENDICATION Procédé pour la préparation d'aldéhydes non saturés, comprenant au moins 7 atomes de carbone, de formule générale I suivante : EMI2.1 dans laquelle les groupes R, Ri, R, Rs, R, Ra, Rg, RTS RR reprsentent l'hydrogène ou des restes aroma- tiques. hétérocycliques ou aliphatiques linéaires ou ramifiés. libres ou reliés entre eux de façon à former des cycles, satures ou non saturés, substitués ou non par des restes aromatiques ou hétérocycliques, caractérisé en ce qu'on condense, en présence d'un catalyseur de condensation, un alcool allylique substitué de formule générale III suivante : EMI2.2 avec un éther vinylique substitué de formule générale II suivante : CLAIM Process for the preparation of unsaturated aldehydes, comprising at least 7 carbon atoms, of the following general formula I: EMI2.1 in which the groups R, Ri, R, Rs, R, Ra, Rg, RTS RR represent hydrogen or aromatic residues. linear or branched heterocyclic or aliphatic. free or linked together so as to form rings, saturated or unsaturated, substituted or not by aromatic or heterocyclic residues, characterized in that, in the presence of a condensation catalyst, a substituted allyl alcohol of formula condenses General III following: EMI2.2 with a substituted vinyl ether of the following general formula II: EMI2.3 dans lesquelles les groupes R à R8 ont la signification définie ci-dessus et R'est un groupe aliphatique, alicyclique, aromatique ou hétérocyclique aisément scindé au cours de la réaction. EMI2.3 in which the groups R to R8 have the meaning defined above and R′s an aliphatic, alicyclic, aromatic or heterocyclic group easily split during the reaction. SOUS-REVENDICATIONS 1. Procédé suivant la revendication, caractérisé en ce qu'on emploie comme catalyseur de condensation un sel d'un métal faisant partie des 4e, Se et 6e périodes des éléments. SUB-CLAIMS 1. Process according to claim, characterized in that a salt of a metal forming part of the 4th, Se and 6th periods of the elements is used as the condensation catalyst. 2. Procédé suivant la revendication et la sous-revendication 1, caractérisé en ce qu'on emploie-un sel de cobalt, d'argent ou de mercure et qu'on opère à une température comprise entre 40 et 160 mais de préfé- rence voisine de 100 . 2. Process according to claim and sub-claim 1, characterized in that a salt of cobalt, silver or mercury is employed and that the operation is carried out at a temperature of between 40 and 160 but preferably. close to 100. 3. Procédé suivant la revendication et les sous-revendictions 1 et 2, caractérisé en ce que le produit obtenu comprend au plus 25 atomes de carbone. 3. Method according to claim and sub-claims 1 and 2, characterized in that the product obtained comprises at most 25 carbon atoms. 4. Procédé suivant la revendication et les sous-revendications 1 et 2, caractérisé en ce qu'on condense l'éther 2-méthylbutadiényl éthylique avec l'alcool crotylique, cette réaction fournissant le 2-méthyloctadien- (2,6) au- (1). 4. A method according to claim and sub-claims 1 and 2, characterized in that condenses 2-methylbutadienyl ethyl ether with crotyl alcohol, this reaction providing 2-methyloctadien- (2,6) au- (1).
CH1365267A 1967-05-26 1967-09-29 Process for the preparation of unsaturated aldehydes CH479515A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CH1365267A CH479515A (en) 1967-05-26 1967-09-29 Process for the preparation of unsaturated aldehydes
CH697268A CH510602A (en) 1967-05-26 1968-05-10 Process for the preparation of carbonyl compounds
US731277A US3654309A (en) 1967-05-26 1968-05-22 Process for the preparation of unsaturated aldehydes
GB1233221D GB1233221A (en) 1967-05-26 1968-05-23
GB1233222D GB1233222A (en) 1967-05-26 1968-05-23
NL6807345A NL6807345A (en) 1967-05-26 1968-05-24
DE19681768552 DE1768552A1 (en) 1967-05-26 1968-05-25 Process for the preparation of unsaturated carbonyl compounds
FR1582515D FR1582515A (en) 1967-05-26 1968-05-27

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH751167A CH473753A (en) 1967-05-26 1967-05-26 Process for the preparation of unsaturated aldehydes
CH1365267A CH479515A (en) 1967-05-26 1967-09-29 Process for the preparation of unsaturated aldehydes

Publications (1)

Publication Number Publication Date
CH479515A true CH479515A (en) 1969-10-15

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CH1365267A CH479515A (en) 1967-05-26 1967-09-29 Process for the preparation of unsaturated aldehydes

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2411530A1 (en) * 1973-03-12 1974-09-26 Hoffmann La Roche METHOD FOR MANUFACTURING ALDEHYDE
EP0037584A1 (en) * 1980-04-09 1981-10-14 Consortium für elektrochemische Industrie GmbH 2,4-Dialkyl-2,6-heptadienals and -hetadienols, process for their preparation and their use as perfume compounds and flavourings
WO2019122232A1 (en) * 2017-12-21 2019-06-27 Firmenich Sa Use of volatile compounds to modulate the perception of musk

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2411530A1 (en) * 1973-03-12 1974-09-26 Hoffmann La Roche METHOD FOR MANUFACTURING ALDEHYDE
EP0037584A1 (en) * 1980-04-09 1981-10-14 Consortium für elektrochemische Industrie GmbH 2,4-Dialkyl-2,6-heptadienals and -hetadienols, process for their preparation and their use as perfume compounds and flavourings
WO2019122232A1 (en) * 2017-12-21 2019-06-27 Firmenich Sa Use of volatile compounds to modulate the perception of musk
US11530366B2 (en) 2017-12-21 2022-12-20 Firmenich Sa Use of volatile compounds to modulate the perception of musk

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