CH156112A - Process for the preparation of a valuable odorous substance. - Google Patents

Process for the preparation of a valuable odorous substance.

Info

Publication number
CH156112A
CH156112A CH156112DA CH156112A CH 156112 A CH156112 A CH 156112A CH 156112D A CH156112D A CH 156112DA CH 156112 A CH156112 A CH 156112A
Authority
CH
Switzerland
Prior art keywords
valuable
preparation
odorous substance
fragrance
pressure
Prior art date
Application number
Other languages
German (de)
Inventor
Kuhn Richard Dr Professor
Original Assignee
Kuhn Richard Dr Professor
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 Kuhn Richard Dr Professor filed Critical Kuhn Richard Dr Professor
Publication of CH156112A publication Critical patent/CH156112A/en

Links

Landscapes

  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Darstellung eines wertvollen Riechstoffes.         flus    den Untersuchungen von R.     guhn     und<B>Al.</B>     Hoffer    (Berliner Berichte 64, 1931,  S. 1243) geht hervor, dass die durch Konden  sation von     Citral-    und     Malonsäure    erhaltene  sogenannte     Citrylidenmalonsäure    in Wirklich  keit ein     Dilacton    der Formel I ist.

   Durch  Einwirkung molekularer Mengen Lauge ent-    steht daraus ein     Ogylacton    der Formel     II.     Dieses gibt durch Behandeln mit einer     halogen-          wasserstoffhaltigen    alkoholischen Lösung, z. B.

    von Salzsäure in     Methylalkohol,    einen     Dichlor-          ester,    den     1,4-Dihalogenmenthaii-3-essigsäure-          methylester    der Formel     III.     
EMI0001.0019     
    Es wurde nun gefunden, dass man zu  einem wertvollen     Riechstoff    gelangen kann,  wenn man     1,4-Dihalpgenmenthan-3-essigsäure-          methylester    bis zur vollständigen Abspaltung  von Halogen in Form von     Halogenwasserstoff     erwärmt.

      Der so erhaltene     Riechstoff    besteht ver  mutlich aus einem Gemisch     isomerer    unge  sättigter Verbindungen mit zwei Doppelbin  dungen. Er bildet ein farbloses 01, das bei  gewöhnlichem Druck bei 244-252   und bei  11 mm Druck bei 135-138   siedet und noch      folgende durchschnittliche Konstanten zeigt:  
EMI0002.0001     
    Der neue Riechstoff soll für     Parfumerie-          zwecke    Verwendung     äinden.     



  <I>Beispiel:</I>       1,4-Dichlormenthan        -3-essigsäuremethyl-          ester    wird unter     Rückfluss    zum gelinden Sie  den erhitzt, bis kein Chlorwasserstoff mehr  entweicht. Durch Destillation des Rückstandes  wird der neue Riechstoff in reinem Zustand  gewonnen.



      Process for the preparation of a valuable odorous substance. According to the investigations by R. Guhn and <B> Al. </B> Hoffer (Berliner Reports 64, 1931, p. 1243) it emerges that the so-called citrylidenemalonic acid obtained by the condensation of citralic and malonic acid is actually a dilactone of formula I.

   The action of molecular amounts of alkali turns it into an ogylactone of the formula II. This is given by treatment with an alcoholic solution containing hydrogen halide, e.g. B.

    of hydrochloric acid in methyl alcohol, a dichloro ester, the 1,4-dihalogen menthali-3-acetic acid methyl ester of the formula III.
EMI0001.0019
    It has now been found that a valuable fragrance can be obtained if methyl 1,4-dihalpgene-3-acetic acid is heated until halogen is completely eliminated in the form of hydrogen halide.

      The fragrance obtained in this way probably consists of a mixture of isomeric unsaturated compounds with two double bonds. It forms a colorless 01, which boils at 244-252 under normal pressure and at 135-138 under 11 mm pressure and still shows the following average constants:
EMI0002.0001
    The new fragrance is intended to be used for perfumery purposes.



  <I> Example: </I> 1,4-dichloromethane -3-acetic acid methyl ester is gently heated under reflux until no more hydrogen chloride escapes. The new fragrance is obtained in a pure state by distilling the residue.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines wertvollen Riechstoffes, dadurch gekennzeichnet, dass man 1,4-Dihalogenmenthan - 3 - essigsäure- methylester bis zur vollständigen Abspaltung von Halogen in Form von Halogenwasserstoff erwärmt. Der so erhaltene Riechstoff bildet ein farb loses Öl, das bei gewöhnlichem Druck bei 244-252' und bei 11 mm Druck bei 135 bis<B>138'</B> siedet und noch folgende durch schnittliche Konstanten zeigt: EMI0002.0014 Der neue Riechstoff soll für Parfumerie- zwecke Verwendung finden. PATENT CLAIM: A process for the preparation of a valuable odorant, characterized in that 1,4-dihalomethane - 3 - methyl acetate is heated until halogen is completely eliminated in the form of hydrogen halide. The fragrance obtained in this way forms a colorless oil that boils at normal pressure at 244-252 'and at 11 mm pressure at 135 to 138' and also shows the following average constants: EMI0002.0014 The new fragrance is to be used for perfumery purposes.
CH156112D 1931-07-21 1931-07-21 Process for the preparation of a valuable odorous substance. CH156112A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH156112T 1931-07-21

Publications (1)

Publication Number Publication Date
CH156112A true CH156112A (en) 1932-07-31

Family

ID=4410521

Family Applications (1)

Application Number Title Priority Date Filing Date
CH156112D CH156112A (en) 1931-07-21 1931-07-21 Process for the preparation of a valuable odorous substance.

Country Status (1)

Country Link
CH (1) CH156112A (en)

Similar Documents

Publication Publication Date Title
CH156112A (en) Process for the preparation of a valuable odorous substance.
DE857802C (en) Process for purifying trimethylolpropane
DE536889C (en) Process for the production of ethers of polynuclear hydrocarbons
DE166899C (en)
DE668255C (en) Process for the production of desiccants
DE402992C (en) Process for the production of odorless naphthenic acid esters
DE646932C (en) Process for the production of diamino alcohols of the fatty aromatic series
DE665792C (en) Process for the production of Diaethylaminoaethanol
DE617879C (en) Process for the preparation of unsaturated amines
DE638393C (en) Process for the production of non-splintering glass
DE244208C (en)
CH194883A (en) Process for the preparation of a compound of theobromine.
CH184313A (en) Means for preventing the formation of moisture fogging and method for the production thereof.
CH135890A (en) Process for the preparation of a basic phenol alkyl ether.
CH199042A (en) Process for the preparation of 5-isopropyl-5-furomethylbarbituric acid.
CH190546A (en) Process for the preparation of 5-benzoylamino-m-phenanthroline.
CH174263A (en) Process for the preparation of methylamino-6-methyl-2-hepten-2.
CH194876A (en) Process for the preparation of 2 (3 &#39;, 5&#39;-Diiodo-2&#39;-B-oxethyl-4&#39;-oxypheny) - 6-iodoquinoline-4-carboxylic acid.
CH212593A (en) Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position.
DE1018175B (en) Process for refining lanolin
CH212595A (en) Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position.
CH187013A (en) Process for the preparation of a cyclic ketone.
CH114009A (en) Method for the preparation of benzylresorcinol.
CH112495A (en) Process for the production of benzylresorcinol.
CH143255A (en) Process for the preparation of a compound with a hydrogenated ring system.