CH304306A - Process for the preparation of a substituted cumalic acid ester. - Google Patents

Process for the preparation of a substituted cumalic acid ester.

Info

Publication number
CH304306A
CH304306A CH304306DA CH304306A CH 304306 A CH304306 A CH 304306A CH 304306D A CH304306D A CH 304306DA CH 304306 A CH304306 A CH 304306A
Authority
CH
Switzerland
Prior art keywords
substituted
preparation
acid ester
ester
water
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 CH304306A publication Critical patent/CH304306A/en

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

Description

  

      Verfahren    zur Herstellung     eines    substituierten     Cumalinsäureesters.       Es wurde gefunden, dass     Cumalinsäuren     und deren Ester, die in 4-     und        6-@Stellung     durch einen     Alkylrest    substituiert sind, ins  besondere solche, bei denen die     Alkylreste     mehr als ein     C-Atom    aufweisen, bemerkens  werte antibakterielle Wirkung zeigen.

   So ver  mag die     4,6-Dibutyl-cumalinsäure    das     Waclis-          tum    von     3ilycobacteriuin        Phlei    in     syntheti-          sehem        Milieu    noch in einer Verdünnung von  15<B>;,</B> pro     eins    zu 90      /o    und dasjenige von       Staphylococcus        aureus    zu 6504, zu hemmen.  Die neuen Verbindungen sollen als Arznei  mittel verwendet werden.  



  Die neuen Verbindungen können in an sich  bekannter Weise durch     Kondensation    der  Homologen des     Acetessigesters    unter dem  Einfluss von     hochkonzentrierten,    vorzugs  weise wasserfreien     Mineralsäuren,    insbeson  dere     Salzsäure    oder Schwefelsäure, erhalten  werden. Die     Kondensation    mit Schwefelsäure  führt zu einem Gemisch von freier Säure  und Ester, das durch fraktionierte Destilla  tion im Hochvakuum getrennt werden kann.  



  Gegenstand des Patentes ist nun ein Ver  fahren zur Herstellung von     4;6-Diäthyl-cuma-          linsäuremethylester,    das dadurch gekennzeich  net ist, dass man auf     Propionyl-essigsäure-          methylester    bei     gewöhnlicher    Temperatur  eine hochkonzentrierte Mineralsäure einwirken  lässt, das Reaktionsprodukt mit Wasser ver  dünnt, die wässerige Lösung mit einem mit  Wasser nicht mischbaren     Lösungsmittel    ex-         trahiert        und    aus dem Extrakt den gesuchten  Ester     isoliert.     



       Beispiel:     8;5 Gewichtsteile     Propionyl-essigsäureme-          thylester    werden mit 20 Gewichtsteilen kon  zentrierter Schwefelsäure versetzt     und    das  Gemisch 10 Tage bei Zimmertemperatur auf  bewahrt. Hernach wird die dunkelbraune Lö  sung in Wasser     ausgegossen    und mit Äther  ausgeschüttelt.

   Der aus der     Ätherlösung    nach  Trocknen     und        Abdampfen    des Äthers erhal  tene Rückstand     liefert    bei der     Destillation    im  Hochvakuum nach einem Vorlauf     4,6-Di-          äthyl-cumalinsäuremethylester        als    gelbes Öl  vom     Siedepunkt    0,1 bis<B>0,15</B> mm 130     bis     135  C.



      Process for the preparation of a substituted cumalic acid ester. It has been found that cumalic acids and their esters which are substituted in the 4- and 6- @ positions by an alkyl radical, in particular those in which the alkyl radicals have more than one carbon atom, show a remarkable antibacterial effect.

   Thus, 4,6-dibutyl-cumalic acid can still manage the growth of 3ilycobacterium Phlei in a synthetic medium in a dilution of 15% per one to 90% and that of Staphylococcus aureus to increase 6504, to inhibit. The new compounds are intended to be used as medicinal products.



  The new compounds can be obtained in a manner known per se by condensation of the homologues of the acetoacetic ester under the influence of highly concentrated, preferably anhydrous mineral acids, in particular hydrochloric acid or sulfuric acid. The condensation with sulfuric acid leads to a mixture of free acid and ester, which can be separated by fractional distillation in a high vacuum.



  The subject of the patent is now a process for the production of 4; 6-diethyl-cumalinic acid methyl ester, which is characterized in that a highly concentrated mineral acid is allowed to act on propionyl-acetic acid methyl ester at normal temperature and the reaction product is diluted with water , extract the aqueous solution with a water-immiscible solvent and isolate the desired ester from the extract.



       Example: 8; 5 parts by weight of methyl propionyl acetate are mixed with 20 parts by weight of concentrated sulfuric acid and the mixture is kept at room temperature for 10 days. Then the dark brown solution is poured into water and shaken out with ether.

   The residue obtained from the ether solution after drying and evaporation of the ether yields methyl 4,6-diethyl-cumalate as a yellow oil with a boiling point of 0.1 to 0.15 in the distillation under high vacuum after a forerun mm 130 to 135 C.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von 4;6-Di- äthyl-cumalinsäuremethylester, dadurch ge kennzeichnet, dass man auf Propionylessig- säuremethylester bei gewöhnlicher Tempera tur eine hochkonzentrierte Mineralsäure ein wirken lässt, tlas Reaktionsprodukt mit Was ser verdünnt, die wässerige Lösung mit einem mit Wasser nicht mischbaren Lösungsmittel extrahiert und aus dem Extrakt den ge suchten Ester isoliert. Die neue Verbindung ist ein gelbes Öl, PATENT CLAIM Process for the production of 4; 6-diethyl-cumalinic acid methyl ester, characterized in that a highly concentrated mineral acid is allowed to act on propionyl acetic acid methyl ester at normal temperature, the reaction product is diluted with water and the aqueous solution is diluted with water The immiscible solvent is extracted and the ester sought is isolated from the extract. The new compound is a yellow oil das bei 130 bis 13!5 C'/0,1 bis<B>0,15</B> mm siedet. that boils at 130 to 13! 5 C '/ 0.1 to <B> 0.15 </B> mm.
CH304306D 1951-10-18 1951-10-18 Process for the preparation of a substituted cumalic acid ester. CH304306A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH300714T 1951-10-18
CH304306T 1951-10-18

Publications (1)

Publication Number Publication Date
CH304306A true CH304306A (en) 1954-12-31

Family

ID=25734278

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304306D CH304306A (en) 1951-10-18 1951-10-18 Process for the preparation of a substituted cumalic acid ester.

Country Status (1)

Country Link
CH (1) CH304306A (en)

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