CH579557A5 - Norsesquiterpene derivs - useful aroma agents, made from norpatchoulenol - Google Patents

Norsesquiterpene derivs - useful aroma agents, made from norpatchoulenol

Info

Publication number
CH579557A5
CH579557A5 CH288473A CH288473A CH579557A5 CH 579557 A5 CH579557 A5 CH 579557A5 CH 288473 A CH288473 A CH 288473A CH 288473 A CH288473 A CH 288473A CH 579557 A5 CH579557 A5 CH 579557A5
Authority
CH
Switzerland
Prior art keywords
norpatchoulenol
formula
known per
epoxidation
compound
Prior art date
Application number
CH288473A
Other languages
German (de)
Original Assignee
Roure Bertrand Dupont 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 Roure Bertrand Dupont Sa filed Critical Roure Bertrand Dupont Sa
Priority to CH288473A priority Critical patent/CH579557A5/en
Priority to DE19742407782 priority patent/DE2407782A1/en
Priority to IT4860374A priority patent/IT1053530B/en
Priority to BR132174A priority patent/BR7401321D0/en
Priority to BR123174A priority patent/BR7401231D0/en
Priority to NL7402595A priority patent/NL7402595A/xx
Priority to GB888374A priority patent/GB1398706A/en
Priority to CA193,680A priority patent/CA1024154A/en
Priority to FR7406597A priority patent/FR2219138B1/fr
Priority to ES423673A priority patent/ES423673A1/en
Priority to JP2322774A priority patent/JPS49134664A/ja
Priority to BE141489A priority patent/BE811693A/en
Publication of CH579557A5 publication Critical patent/CH579557A5/en
Priority to US05/723,748 priority patent/US4083812A/en
Priority to US05/723,749 priority patent/US4064060A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
    • C07C49/507—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic
    • C07C49/513—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • 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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings

Landscapes

  • 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)
  • Epoxy Compounds (AREA)

Abstract

Title cpds. are of formula (I): in which either (a) R1-R4 = H or two of R1-R4 = and the other two together = 0, or (b) three of R1-R4 = H and the fourth = CH. They are made from norpatchoulenol (II): by epoxidation, oxidation and reduction processes. The prods. are useful as perfume agents in soaps, detergents, toilet requisits, etc.

Description

  

  
 



   Die Erfindung betrifft ein Verfahren zur Herstellung eines Epoxyalkohols der Formel
EMI1.1     
 welches dadurch gekennzeichnet ist, dass man Norpatchoulenol der Formel
EMI1.2     
 der Epoxydation unterwirft.



   Die erfindungsgemäss erhaltene Verbindung der Formel I kann als Riechstoff und/oder als Zwischenprodukt zur Herstellung von solchen verwendet werden. Sie besitzt zum Teil auch fixierende Eigenschaften. Ihr Geruch kann als camphrig, modrig, holzig umschrieben werden. Sie kann auf an sich bekannte Art mit andern Riechstoffen zu Riechstoffkompositionen (z.B. Parfumbasen) kombiniert werden, wobei der Gehalt in solchen Kompositionen innerhalb weiter Grenzen, z.B. zwischen etwa 1 und 20   Gew.- %    variieren kann. Riechstoffkompositionen mit einem Gehalt an der Verbindung der Formel I können als Parfums oder zur Par   fümierung    von kosmetischen Produkten (Seifen, Toilettewassern, Cremes etc.) sowie z.B. von Reinigungsmitteln (Detergentien, Waschmittel etc.) verwendet werden.



   Das erfindungsgemäss zur Herstellung der Verbindung I befolgte Verfahren ist an sich bekannt. Der als Ausgangsstoff dienende ungesättigte   tricyclische    Alkohol (Norde   hydropatchoulol bzw.    Norpatchoulenol) kommt in natürlichem Patchouliöl vor und kann daraus nach an sich bekannten Methoden isoliert werden (vgl. deutsche Offenlegungsschrift 2 242 913).



   Die Epoxydation von Norpatchoulenol II kann auf an sich bekannte Art mittels einer Persäure, wie Perphthalsäure, Perbenzoesäure, vorzugsweise aber mit der leicht erhältlichen Peressigsäure durchgeführt werden.



   Beispiel
In einen 500 ml-Kolben gibt man 1 g (4,8 mMol) Norpatchoulenol, gelöst in 50 ml Methylenchlorid, und 1 g trokkenes Natriumacetat. Die so erhaltene Suspension wird kräftig gerührt, abgekühlt und dann mit 15 ml 35%iger Peressigsäure versetzt. Man überlasst das Gemisch hierauf während 48 Stunden der Raumtemperatur, wonach das Norpatchoulenol praktisch verschwunden ist. Nach Zugabe von 300 ml Wasser wird die Reaktionsmasse mit Methylenchlorid extrahiert. Dann werden die organischen Extrakte mit 9%iger Natriumbicarbonatlösung, hierauf mit 10%-iger Natriumsulfitlösung und schliesslich mit Wasser neutral gewaschen. Die getrocknete Lösung wird durch Destillation vom Lösungsmittel befreit. Man erhält so 1,05 g kristallisierten, rohen Epoxyalkohol der Formel I.

  Die Substanz kann durch Chromatographie an Silicagel und   Vacuumsublimation    analytisch rein erhalten werden (Ausbeute 90%) und zeigt dann die folgenden Konstanten:    [ S25 (CHCl3) = +29,7    
Massenspektrum:   C14H22O2    (M = 222)
222 (M); 207 (M-CH3); 204 (M-H2O); 189 (M-H2O-CH3); 179 (M-C3H7); 166; 161   (M-H2O-C3H);    138; 95; 84 IR-Spektrum:    y xBr      (cm-1):    3520; 3620; 3460; 3000; 1465; 1380-1365;
1305; 1060-1040; 1030;   980;    950-870-810;
753; 740 NMR-Spektrum:   (iu    8 Einheiten)
0,89; 1,01; 1,11; 2,80; 3,01.

 

   PATENTANSPRUCH



   Verfahren zur Herstellung eines Epoxyalkohols der Formel
EMI1.3     
 dadurch gekennzeichnet, dass man Norpatchoulenol der Formel
EMI1.4     
 der Epoxydation unterwirft.

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.



   



  
 



   The invention relates to a process for the preparation of an epoxy alcohol of the formula
EMI1.1
 which is characterized in that one norpatchoulenol of the formula
EMI1.2
 subject to epoxidation.



   The compound of the formula I obtained according to the invention can be used as a fragrance and / or as an intermediate for the production of such. It also has some fixing properties. Their smell can be described as camphor, musty, woody. It can be combined in a manner known per se with other fragrances to form fragrance compositions (e.g. perfume bases), the content in such compositions being within wide limits, e.g. can vary between about 1 and 20% by weight. Fragrance compositions containing the compound of the formula I can be used as perfumes or for perfuming cosmetic products (soaps, toilet waters, creams, etc.) and e.g. cleaning agents (detergents, laundry detergents, etc.).



   The process followed according to the invention for the preparation of the compound I is known per se. The unsaturated tricyclic alcohol (Norde hydropatchoulol or norpatchoulenol) used as the starting material occurs in natural patchouli oil and can be isolated therefrom by methods known per se (cf. German laid-open specification 2 242 913).



   The epoxidation of norpatchoulenol II can be carried out in a manner known per se using a peracid such as perphthalic acid or perbenzoic acid, but preferably using the readily available peracetic acid.



   example
1 g (4.8 mmol) of norpatchoulenol, dissolved in 50 ml of methylene chloride, and 1 g of dry sodium acetate are placed in a 500 ml flask. The suspension obtained in this way is stirred vigorously, cooled and then mixed with 15 ml of 35% strength peracetic acid. The mixture is then left to room temperature for 48 hours, after which the norpatchoulenol has practically disappeared. After adding 300 ml of water, the reaction mass is extracted with methylene chloride. The organic extracts are then washed neutral with 9% sodium bicarbonate solution, then with 10% sodium sulfite solution and finally with water. The dried solution is freed from the solvent by distillation. This gives 1.05 g of crystallized, crude epoxy alcohol of the formula I.

  The substance can be obtained analytically pure by chromatography on silica gel and vacuum sublimation (yield 90%) and then shows the following constants: [S25 (CHCl3) = +29.7
Mass spectrum: C14H22O2 (M = 222)
222 (M); 207 (M-CH3); 204 (M-H2O); 189 (M-H2O-CH3); 179 (M-C3H7); 166; 161 (M-H2O-C3H); 138; 95; 84 IR spectrum: y xBr (cm-1): 3520; 3620; 3460; 3000; 1465; 1380-1365;
1305; 1060-1040; 1030; 980; 950-870-810;
753; 740 NMR Spectrum: (iu 8 units)
0.89; 1.01; 1.11; 2.80; 3.01.

 

   PATENT CLAIM



   Process for the preparation of an epoxy alcohol of the formula
EMI1.3
 characterized in that one has norpatchoulenol of the formula
EMI1.4
 subject to epoxidation.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Die Erfindung betrifft ein Verfahren zur Herstellung eines Epoxyalkohols der Formel EMI1.1 welches dadurch gekennzeichnet ist, dass man Norpatchoulenol der Formel EMI1.2 der Epoxydation unterwirft. The invention relates to a process for the preparation of an epoxy alcohol of the formula EMI1.1 which is characterized in that one norpatchoulenol of the formula EMI1.2 subject to epoxidation. Die erfindungsgemäss erhaltene Verbindung der Formel I kann als Riechstoff und/oder als Zwischenprodukt zur Herstellung von solchen verwendet werden. Sie besitzt zum Teil auch fixierende Eigenschaften. Ihr Geruch kann als camphrig, modrig, holzig umschrieben werden. Sie kann auf an sich bekannte Art mit andern Riechstoffen zu Riechstoffkompositionen (z.B. Parfumbasen) kombiniert werden, wobei der Gehalt in solchen Kompositionen innerhalb weiter Grenzen, z.B. zwischen etwa 1 und 20 Gew.- % variieren kann. Riechstoffkompositionen mit einem Gehalt an der Verbindung der Formel I können als Parfums oder zur Par fümierung von kosmetischen Produkten (Seifen, Toilettewassern, Cremes etc.) sowie z.B. von Reinigungsmitteln (Detergentien, Waschmittel etc.) verwendet werden. The compound of the formula I obtained according to the invention can be used as a fragrance and / or as an intermediate for the production of such. It also has some fixing properties. Their smell can be described as camphor, musty, woody. It can be combined in a manner known per se with other fragrances to form fragrance compositions (e.g. perfume bases), the content in such compositions being within wide limits, e.g. can vary between about 1 and 20% by weight. Fragrance compositions containing the compound of the formula I can be used as perfumes or for perfuming cosmetic products (soaps, toilet waters, creams, etc.) and e.g. cleaning agents (detergents, laundry detergents, etc.). Das erfindungsgemäss zur Herstellung der Verbindung I befolgte Verfahren ist an sich bekannt. Der als Ausgangsstoff dienende ungesättigte tricyclische Alkohol (Norde hydropatchoulol bzw. Norpatchoulenol) kommt in natürlichem Patchouliöl vor und kann daraus nach an sich bekannten Methoden isoliert werden (vgl. deutsche Offenlegungsschrift 2 242 913). The process followed according to the invention for the preparation of the compound I is known per se. The unsaturated tricyclic alcohol (Norde hydropatchoulol or norpatchoulenol) used as the starting material occurs in natural patchouli oil and can be isolated therefrom by methods known per se (cf. German laid-open specification 2 242 913). Die Epoxydation von Norpatchoulenol II kann auf an sich bekannte Art mittels einer Persäure, wie Perphthalsäure, Perbenzoesäure, vorzugsweise aber mit der leicht erhältlichen Peressigsäure durchgeführt werden. The epoxidation of norpatchoulenol II can be carried out in a manner known per se using a peracid such as perphthalic acid or perbenzoic acid, but preferably using the readily available peracetic acid. Beispiel In einen 500 ml-Kolben gibt man 1 g (4,8 mMol) Norpatchoulenol, gelöst in 50 ml Methylenchlorid, und 1 g trokkenes Natriumacetat. Die so erhaltene Suspension wird kräftig gerührt, abgekühlt und dann mit 15 ml 35%iger Peressigsäure versetzt. Man überlasst das Gemisch hierauf während 48 Stunden der Raumtemperatur, wonach das Norpatchoulenol praktisch verschwunden ist. Nach Zugabe von 300 ml Wasser wird die Reaktionsmasse mit Methylenchlorid extrahiert. Dann werden die organischen Extrakte mit 9%iger Natriumbicarbonatlösung, hierauf mit 10%-iger Natriumsulfitlösung und schliesslich mit Wasser neutral gewaschen. Die getrocknete Lösung wird durch Destillation vom Lösungsmittel befreit. Man erhält so 1,05 g kristallisierten, rohen Epoxyalkohol der Formel I. example 1 g (4.8 mmol) of norpatchoulenol, dissolved in 50 ml of methylene chloride, and 1 g of dry sodium acetate are placed in a 500 ml flask. The suspension obtained in this way is stirred vigorously, cooled and then mixed with 15 ml of 35% strength peracetic acid. The mixture is then left to room temperature for 48 hours, after which the norpatchoulenol has practically disappeared. After adding 300 ml of water, the reaction mass is extracted with methylene chloride. The organic extracts are then washed neutral with 9% sodium bicarbonate solution, then with 10% sodium sulfite solution and finally with water. The dried solution is freed from the solvent by distillation. This gives 1.05 g of crystallized, crude epoxy alcohol of the formula I. Die Substanz kann durch Chromatographie an Silicagel und Vacuumsublimation analytisch rein erhalten werden (Ausbeute 90%) und zeigt dann die folgenden Konstanten: [ S25 (CHCl3) = +29,7 Massenspektrum: C14H22O2 (M = 222) 222 (M); 207 (M-CH3); 204 (M-H2O); 189 (M-H2O-CH3); 179 (M-C3H7); 166; 161 (M-H2O-C3H); 138; 95; 84 IR-Spektrum: y xBr (cm-1): 3520; 3620; 3460; 3000; 1465; 1380-1365; 1305; 1060-1040; 1030; 980; 950-870-810; 753; 740 NMR-Spektrum: (iu 8 Einheiten) 0,89; 1,01; 1,11; 2,80; 3,01. The substance can be obtained analytically pure by chromatography on silica gel and vacuum sublimation (yield 90%) and then shows the following constants: [S25 (CHCl3) = +29.7 Mass spectrum: C14H22O2 (M = 222) 222 (M); 207 (M-CH3); 204 (M-H2O); 189 (M-H2O-CH3); 179 (M-C3H7); 166; 161 (M-H2O-C3H); 138; 95; 84 IR spectrum: y xBr (cm-1): 3520; 3620; 3460; 3000; 1465; 1380-1365; 1305; 1060-1040; 1030; 980; 950-870-810; 753; 740 NMR Spectrum: (iu 8 units) 0.89; 1.01; 1.11; 2.80; 3.01. PATENTANSPRUCH PATENT CLAIM Verfahren zur Herstellung eines Epoxyalkohols der Formel EMI1.3 dadurch gekennzeichnet, dass man Norpatchoulenol der Formel EMI1.4 der Epoxydation unterwirft. Process for the preparation of an epoxy alcohol of the formula EMI1.3 characterized in that one has norpatchoulenol of the formula EMI1.4 subject to epoxidation.
CH288473A 1973-02-28 1973-02-28 Norsesquiterpene derivs - useful aroma agents, made from norpatchoulenol CH579557A5 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
CH288473A CH579557A5 (en) 1973-02-28 1973-02-28 Norsesquiterpene derivs - useful aroma agents, made from norpatchoulenol
DE19742407782 DE2407782A1 (en) 1973-02-28 1974-02-19 NORSESQUITERPENDERIVATE
IT4860374A IT1053530B (en) 1973-02-28 1974-02-20 NORSESQUITERPENI DERIVATIVES
BR132174A BR7401321D0 (en) 1973-02-28 1974-02-22 PROCESS FOR THE PREPARATION OF NOR-SESQUITERPEN DERIVATIVES, AND PROCESS FOR PERFUMING PRODUCTS
BR123174A BR7401231D0 (en) 1973-02-28 1974-02-22 PROCESS FOR THE PREPARATION OF NOR-SESQUITERPEN DERIVATIVES, AND PROCESS FOR PERFUMING PRODUCTS
NL7402595A NL7402595A (en) 1973-02-28 1974-02-26
CA193,680A CA1024154A (en) 1973-02-28 1974-02-27 Nor-sesquiterpene derivatives
GB888374A GB1398706A (en) 1973-02-28 1974-02-27 Nor-sesquiterpene derivatives
FR7406597A FR2219138B1 (en) 1973-02-28 1974-02-27
ES423673A ES423673A1 (en) 1973-02-28 1974-02-27 Nor-sesquiterpene derivatives
JP2322774A JPS49134664A (en) 1973-02-28 1974-02-27
BE141489A BE811693A (en) 1973-02-28 1974-02-28 NOR- SESQUITERPENE DERIVATIVES
US05/723,748 US4083812A (en) 1973-02-28 1976-09-16 Certain ketoalcohol tricyclic norsesquiterpene derivatives and compositions containing the same
US05/723,749 US4064060A (en) 1973-02-28 1976-09-16 Epoxy alcohol tricyclic norsesquiterpene derivative and compositions containing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH288473A CH579557A5 (en) 1973-02-28 1973-02-28 Norsesquiterpene derivs - useful aroma agents, made from norpatchoulenol

Publications (1)

Publication Number Publication Date
CH579557A5 true CH579557A5 (en) 1976-09-15

Family

ID=4243754

Family Applications (1)

Application Number Title Priority Date Filing Date
CH288473A CH579557A5 (en) 1973-02-28 1973-02-28 Norsesquiterpene derivs - useful aroma agents, made from norpatchoulenol

Country Status (3)

Country Link
BE (1) BE811693A (en)
BR (2) BR7401231D0 (en)
CH (1) CH579557A5 (en)

Also Published As

Publication number Publication date
BR7401321D0 (en) 1974-11-05
BE811693A (en) 1974-08-28
BR7401231D0 (en) 1974-11-05

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