CH299536A - Method for making a derivative of pyran. - Google Patents

Method for making a derivative of pyran.

Info

Publication number
CH299536A
CH299536A CH299536DA CH299536A CH 299536 A CH299536 A CH 299536A CH 299536D A CH299536D A CH 299536DA CH 299536 A CH299536 A CH 299536A
Authority
CH
Switzerland
Prior art keywords
caprylyl
pyran
derivative
dihydropyran
heptyl
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH299536A publication Critical patent/CH299536A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines     Pyranabkömmlings.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     Pyranderiv        a-          ten    der allgemeinen Formel  
EMI0001.0005     
    wobei R einen     geradkettigen,    verzweigten       Alkyl-    oder     Alkenylrest    mit.

   mehr-als 5     C-          Atomen    bedeutet, das dadurch gekennzeichnet  ist, dass man homologe     Acetessigester    von der  Formel       R-CO-CH2-COOR',     wobei R die oben angegebene Bedeutung zu  kommt und R' einen beliebigen niederen     Alkyl-          rest    darstellt, bei Gegenwart eines basisch  reagierenden Katalysators, vornehmlich     Na-          triumbicarbonat,    auf 200-220  C erhitzt und       den,

      bei der Reaktion sich bildenden Alkohol       abdestilliert.    Die neuen     Verbindungen    weisen  gärungshemmende und     bactericide        Wirkung     auf und sind sehr wenig toxisch für den  Warmblüter.  



       Gegenstand    des Patentes ist ein Verfahren  zur Herstellung von     3-Caprylyl-6-heptyl-2,3-          dihydropyran-2,4-dion,    welches dadurch ge-    kennzeichnet ist, dass man' einen     Caprylyl-          essigsäureester    der Formel       CI3-(CH2)6-CO    '     CH2-COOR,     worin R einen niederen     Alkylrest    darstellt,  bei Gegenwart eines basisch reagierenden  Katalysators auf 200-220  erhitzt und den  bei der Reaktion sich bildenden Alkohol ab  destilliert.  



  Die neue     Verbindung    soll als     Desinfek-          tions-    und     Heilmittel        Verwendung    finden.  <I>Beispiel:</I>  100 Gewichtsteile     Caprylylessigsäureme-          thylester        (Kp16    136-138 ) werden mit 0,10  Gewichtsteilen     Natriumbicarbonat    drei Stun  den bei 210-215  C erhitzt, wobei 9,5 Ge  wichtsteile Alkohol     abdestillieren.        Ein    bei  0,2 mm     Hg    unterhalb 120  siedender Vorlauf  wird     abdestilliert,

      und der     Destillationsrück-          stand    wird aus absolutem Alkohol umkristal  lisiert. Das     3-Caprylyl-6-heptyl-2,3-dihydro-          pyran-2,4-dion    bildet farblose Kristalle vom       Schmelzpunkt    62-63  C.



  Method for making a derivative of pyran. The present invention relates to a process for the preparation of pyran derivatives of the general formula
EMI0001.0005
    where R is a straight-chain, branched alkyl or alkenyl radical.

   Means more than 5 carbon atoms, which is characterized in that homologous acetoacetic esters of the formula R-CO-CH2-COOR ', where R has the meaning given above and R' represents any lower alkyl radical, at The presence of a basic catalyst, primarily sodium bicarbonate, is heated to 200-220 C and the

      alcohol formed during the reaction is distilled off. The new compounds have a fermentation-inhibiting and bactericidal effect and are very little toxic to warm-blooded animals.



       The subject of the patent is a process for the preparation of 3-caprylyl-6-heptyl-2,3-dihydropyran-2,4-dione, which is characterized in that 'a caprylyl acetic acid ester of the formula CI3- (CH2) 6-CO 'CH2-COOR, in which R is a lower alkyl radical, heated to 200-220 in the presence of a basic catalyst and the alcohol formed in the reaction is distilled off.



  The new compound is to be used as a disinfectant and remedy. <I> Example: </I> 100 parts by weight of methyl caprylyl acetate (bp 16 136-138) are heated with 0.10 parts by weight of sodium bicarbonate for three hours at 210-215 ° C., with 9.5 parts by weight of alcohol being distilled off. A forerun boiling at 0.2 mm Hg below 120 is distilled off,

      and the distillation residue is recrystallized from absolute alcohol. The 3-caprylyl-6-heptyl-2,3-dihydropyran-2,4-dione forms colorless crystals with a melting point of 62-63 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3-Capry- lyl-6-heptyl-2,3-dihydropyran-2,4-dion, da durch gekennzeichnet, dass man einen Capry- lylessigsäureester der Formel CH3-(CH2)6-CO # C1: PATENT CLAIM: A process for the preparation of 3-caprylyl-6-heptyl-2,3-dihydropyran-2,4-dione, characterized in that a caprylylacetic acid ester of the formula CH3- (CH2) 6-CO # C1 : 12-COOR, worin R einen niederen Alkylrest darstellt, bei Gegenwart eines basisch reagierenden Ka- talysators auf 200-220 erhitzt und den bei der Reaktion sich bildenden Alkohol abdestil- liert. 3-Caprylyl-6-heptyl-2,3-dihydropyran-2,4- dion bildet farblose Kristalle, die bei 62-63 schmelzen. UNTERANSPRUCH: 12-COOR, where R is a lower alkyl radical, heated to 200-220 in the presence of a basic catalyst and the alcohol formed during the reaction is distilled off. 3-Caprylyl-6-heptyl-2,3-dihydropyran-2,4-dione forms colorless crystals that melt at 62-63. SUBClaim: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass Natriumbicarbonat als Katalysator verwendet wird. J Method according to claim, characterized in that sodium bicarbonate is used as a catalyst. J
CH299536D 1950-03-02 1950-03-02 Method for making a derivative of pyran. CH299536A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH299536T 1950-03-02

Publications (1)

Publication Number Publication Date
CH299536A true CH299536A (en) 1954-06-15

Family

ID=4490350

Family Applications (1)

Application Number Title Priority Date Filing Date
CH299536D CH299536A (en) 1950-03-02 1950-03-02 Method for making a derivative of pyran.

Country Status (1)

Country Link
CH (1) CH299536A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0365539A4 (en) * 1987-06-17 1990-12-05 Australian Commercial Research & Development Limited Human leucocyte elastase inhibitor compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0365539A4 (en) * 1987-06-17 1990-12-05 Australian Commercial Research & Development Limited Human leucocyte elastase inhibitor compounds

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