EP0214588A2 - Oxime cyclique - Google Patents

Oxime cyclique Download PDF

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Publication number
EP0214588A2
EP0214588A2 EP86112050A EP86112050A EP0214588A2 EP 0214588 A2 EP0214588 A2 EP 0214588A2 EP 86112050 A EP86112050 A EP 86112050A EP 86112050 A EP86112050 A EP 86112050A EP 0214588 A2 EP0214588 A2 EP 0214588A2
Authority
EP
European Patent Office
Prior art keywords
oxime
oil
givaudan
ethyl
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP86112050A
Other languages
German (de)
English (en)
Other versions
EP0214588B1 (fr
EP0214588A3 (en
Inventor
Roman Kaiser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
L Givaudan and Co SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L Givaudan and Co SA filed Critical L Givaudan and Co SA
Publication of EP0214588A2 publication Critical patent/EP0214588A2/fr
Publication of EP0214588A3 publication Critical patent/EP0214588A3/de
Application granted granted Critical
Publication of EP0214588B1 publication Critical patent/EP0214588B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms

Definitions

  • the invention relates to a new fragrance. It is the 2- (1'-hydroximino-ethyl) -1,3,3,4,4-pentamethylcyclopentene, that is to say the compound of the formula
  • Formula I is intended to encompass both geometric isomers, ie the syn and anti forms of oxime I.
  • the invention further relates to a process for the preparation of the compounds I.
  • This process is characterized in that 2- acetyl-1,3,3,4,4-pentamethylcyclopentene, ie the ketone of the formula reacted with hydroxylamine or one of its salts.
  • reaction of the compound of formula II with hydroxylamine or a salt thereof can be carried out according to methods known per se, see e.g. Organics, basic organic chemistry internship, author collective; 7th edition; VEB German Publishing House of Sciences; Berlin 1967, 375, 555: the hydroxylamine is conveniently left in the form of a salt, e.g. react as hydrochloride or sulfate, in the presence of a base such as pyridine, sodium acetate, potassium acetate, etc., preferably in alcoholic solution with the ketone I; the reaction temperature is preferably the reflux temperature of the reaction mixture.
  • a salt e.g. react as hydrochloride or sulfate
  • a base such as pyridine, sodium acetate, potassium acetate, etc.
  • the reaction temperature is preferably the reflux temperature of the reaction mixture.
  • the processing is expediently carried out according to methods known per se: distilling off most of the alcohol, adding an organic solvent, washing with water and finally removing the unreacted ketone.
  • the A usgangsketon II is known: for example, describes M. Kolobielski in Ann. Chim. 10, No. 12, (1955), 271 seq.
  • the reductive dimerization of mesityl oxide with magnesium in acetic acid which results in a mixture consisting of 2-acetyl-l, 3,3,4,4-pentamethylcyclopentanol II 'as the main component and smaller amounts of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene (II), 3,5-dimethyl-3 - (2'-methyl-1'-propene-1'- yl) -4-hexen-2-one or 2,4,6-trimethyl-4-acetyl-2,5-heptadiene (IIb), 2,3,3,5-tetramethyl-2-isobutenyl-2, 3-dihydrofuran (II ") and 2,4,5,7-tetramethyl-2,6-octadiene-4,5-diol (II"')
  • a II-rich product can now easily be obtained by treating the product mixture mentioned with a base, such as aqueous sodium hydroxide solution, and working up the acidified reaction mixture.
  • a base such as aqueous sodium hydroxide solution
  • the remaining after distilling off the more volatile compounds of product now includes, for example, 67% I I addition to the acyclic ketones IIb (about 15%), IIc (about 7%) and IId (about 8%)
  • the compound I or the oxime mixture described above, has special organoleptic properties which make it particularly suitable as a fragrance.
  • the invention accordingly also relates to the use of the compound I or its mixture with the above acyclic oximes Ib-Id as a fragrance.
  • the oxime or oxime mixture according to the invention is distinguished by a special combination of valuable properties. It is colorless, easily accessible, the individual approaches are constant in smell, not irritating, stable and easy to use.
  • the compound of formula I has in particular the characteristic smell aspect of the fresh flowers of Salvia sclarea (clary sage), this smell is accompanied by herbaceous nuances.
  • organoleptic properties of I are therefore completely different from the organoleptic properties of this known oxime.
  • Another important and typical property of the new oxime I according to the invention is its high integration capacity in the creation of perfume compositions.
  • the new oxime I develops its full effect particularly in the medium to volatile range of composition by enriching, harmonizing or harmonizing the desired odor complexes modified and fixed the same excellent.
  • compositions produced with I can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, extras, lotions, creams, shampoos, soaps, ointments, powders, deodorants, detergents, tobacco, etc.).
  • the content of I in (new) perfumery bases can easily be up to 80% and in the perfumery compositions thus produced, up to 20-30% of this base can be used without problems to achieve the desired effects.
  • the experienced perfumer can achieve interesting odor nuances with concentrations of 0.1 - 0.5%, so that the concentrations used cover a fairly large range.
  • compositions made with I can be used for all types of perfumed consumer goods.
  • the compounds I can accordingly be used in the production of compositions and - as the above compilation shows - using a wide range of known fragrances.
  • the known fragrances listed above can be used in a manner known to the perfumer, e.g. from W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall, London, 1974.
  • the oxime product mixture thus obtained is separated into the individual constituents by column chromatography on a 100-fold amount of silica gel using hexane / ether 10: 1 as the eluent.
  • the "new compound I" is always understood to mean a mixture of I in combination with the acyclic oximes, as is the case, for example, is accessible according to example 1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Medicinal Preparation (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP86112050A 1985-09-13 1986-09-01 Oxime cyclique Expired - Lifetime EP0214588B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3974/85 1985-09-13
CH397485 1985-09-13

Publications (3)

Publication Number Publication Date
EP0214588A2 true EP0214588A2 (fr) 1987-03-18
EP0214588A3 EP0214588A3 (en) 1988-02-03
EP0214588B1 EP0214588B1 (fr) 1990-09-26

Family

ID=4267438

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86112050A Expired - Lifetime EP0214588B1 (fr) 1985-09-13 1986-09-01 Oxime cyclique

Country Status (4)

Country Link
US (1) US4678604A (fr)
EP (1) EP0214588B1 (fr)
JP (1) JPS6267060A (fr)
DE (1) DE3674517D1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993013054A1 (fr) * 1991-12-20 1993-07-08 Union Camp Corporation Composes nitrile et aldoxime indane, et leur emploi comme parfum
EP0672746A1 (fr) * 1994-03-18 1995-09-20 Givaudan-Roure (International) S.A. Ethers d'oximes et compositions parfumantes et aromatisantes les contenant

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019076933A1 (fr) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Odorisants et compositions comprenant des odorisants

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2433941A1 (fr) * 1978-08-21 1980-03-21 Givaudan & Cie Sa Compositions odorantes
EP0045861A2 (fr) * 1980-08-08 1982-02-17 L. GIVAUDAN & CIE Société Anonyme Composés insaturés, leur procédé de préparation, leur utilisation comme parfums ainsi que les compositions parfumantes les contenant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1205534B (de) * 1962-04-11 1965-11-25 Edison Soc Verfahren zur Herstellung von Cycloalkanonoximen mit 5 bis 12 Ring-kohlenstoffatomen
DE3129934C2 (de) * 1981-07-29 1983-09-15 Dragoco Gerberding & Co Gmbh, 3450 Holzminden Verwendung von 1,5-Dymethyl-8-hydroximino-bicyclo[3.2.1]octan als Riech- und Aromastoff
DE3361874D1 (en) * 1982-02-03 1986-03-06 Givaudan & Cie Sa Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2433941A1 (fr) * 1978-08-21 1980-03-21 Givaudan & Cie Sa Compositions odorantes
EP0045861A2 (fr) * 1980-08-08 1982-02-17 L. GIVAUDAN & CIE Société Anonyme Composés insaturés, leur procédé de préparation, leur utilisation comme parfums ainsi que les compositions parfumantes les contenant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, Nr. 5, 1961, Seiten 1005-1007, Paris, FR; J. WIEMANN et al.: "Sélectivité dans la transposition de Beckmann. Application à l'oxime du pentaméthyl-1,3,3,4,4, acétyl-2 cyclopentène" *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993013054A1 (fr) * 1991-12-20 1993-07-08 Union Camp Corporation Composes nitrile et aldoxime indane, et leur emploi comme parfum
EP0672746A1 (fr) * 1994-03-18 1995-09-20 Givaudan-Roure (International) S.A. Ethers d'oximes et compositions parfumantes et aromatisantes les contenant

Also Published As

Publication number Publication date
EP0214588B1 (fr) 1990-09-26
JPS6267060A (ja) 1987-03-26
EP0214588A3 (en) 1988-02-03
US4678604A (en) 1987-07-07
DE3674517D1 (de) 1990-10-31

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