CH230446A - Process for the preparation of a new ester of the oxy-stilbene series. - Google Patents

Process for the preparation of a new ester of the oxy-stilbene series.

Info

Publication number
CH230446A
CH230446A CH230446DA CH230446A CH 230446 A CH230446 A CH 230446A CH 230446D A CH230446D A CH 230446DA CH 230446 A CH230446 A CH 230446A
Authority
CH
Switzerland
Prior art keywords
diethyl
preparation
ester
oxy
dioxystilbene
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH230446A publication Critical patent/CH230446A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  <B>Zusatzpatent</B>     zum        Hauptpatent        Nm.    225257.    Verfahren zur Darstellung eines neuen Esters der     Oay-stilbenreihe.       Es wurde gefunden, dass man zu einem  neuen Ester gelangen     kann,    wenn man     a,ä        -          Diäthyl-4,4'-dioxystilben    mit einem     Halogen-          ameisensäureäthylester    behandelt.  



  Als     Halogenameisensäureäthy        lester    lässt  sich zum Beispiel     Chlorameisensäureäthyl-          ester    verwenden.  



  Die so erhaltene neue Verbindung, der     Di-          äthylkohlensäureester    des     a,a'-Diäthyl-4,4'-          dioxystilbens,    schmilzt bei 118 . Sie zeigt  gegenüber den bekannten hormonal wirk  samen Verbindungen ohne Steroidcharakter  eine     protrahiertere    Wirkung     im        Oestrus-    und       Uter        uswachstumstest    und soll deshalb thera  peutische Verwendung finden.  



  <I>Beispiel:</I>  Zu einem in Eis gekühlten Gemisch von  1 Teil     a.,a'-Diäthyl-4,4'-dioxystilben    in 2 Tei  len     Pyridin    werden tropfenweise und unter  Rühren 2 Teile     Chlorameisensäureäthylester     gegeben. Die     entstandene    gelbe Mischung    wird im Wasserbad bis zur     Entfärbung     mässig erwärmt und darauf einige     Stunden     bei Zimmertemperatur stehen gelassen.

   Der  entstandene     gristallbiei    wird dann     in    Was  ser und Äther aufgenommen, und die äthe  rische Lösung     nacheinander    mit verdünnter  Schwefelsäure, Wasser,     verdünnter    Natron  lauge und nochmals mit Wasser gewaschen.  Nach dem Trocknen und Verdampfen der  ätherischen     Lösung    erhält man den     Di-äthyl-          kohlensäureester    des     a,ä        -Diäthyl-4,4'-dioxy-          stilbens    als     weissen    kristallinischen Rück  stand. Aus Äthanol umgelöst, schmilzt er  bei 118 .



  <B> Additional patent </B> to the main patent Nm. 225257. Process for the preparation of a new ester of the Oay stilbene series. It has been found that a new ester can be obtained if a, a - diethyl-4,4'-dioxystilbene is treated with an ethyl halide formate.



  As ethyl haloformate, for example ethyl chloroformate can be used.



  The new compound thus obtained, the diethyl carbonic acid ester of a, a'-diethyl-4,4'-dioxystilbene, melts at 118. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterus growth test and should therefore be used therapeutically.



  <I> Example: </I> To a mixture, cooled in ice, of 1 part of a., A'-diethyl-4,4'-dioxystilbene in 2 parts of pyridine, 2 parts of ethyl chloroformate are added dropwise and with stirring. The resulting yellow mixture is moderately warmed in a water bath until it becomes discolored and then left to stand for a few hours at room temperature.

   The resulting granule is then absorbed in water and ether, and the ethereal solution is washed successively with dilute sulfuric acid, water, dilute sodium hydroxide and again with water. After drying and evaporation of the ethereal solution, the diethyl carbonic acid ester of a, ä -diethyl-4,4'-dioxy-stilbene is obtained as a white crystalline residue. Dissolved from ethanol, it melts at 118.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man a,ä -Diäthyl-4,4'-dioxystilben mit einem Ila- logenameisensäureäthylester behandelt. Die so erhaltene neue Verbindung, der Di- äthylkohlensäureester des a,a'-Diäthyl-4,4'- dioxystilbens, schmilzt bei 118 . PATENT CLAIM: Process for the preparation of a new ester, characterized in that a, a -diethyl-4,4'-dioxystilbene is treated with an ethyl ilogenoformate. The new compound thus obtained, the diethyl carbonic acid ester of a, a'-diethyl-4,4'-dioxystilbene, melts at 118. Sie zeigt gegenüber den bekannten hormonal wirk samen Verbindungen ohne Steroidcharakter eine protrahiertere Wirkung im Oestrus- und Uteruswachstumstest und soll deshalb thera peutische Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, daB als Halogenameisen säureäthylester Chlorameisensäureäthylester verwendet wird. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterus growth test and should therefore be used therapeutically. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that ethyl chloroformate is used as the halogen formic acid ethyl ester.
CH230446D 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series. CH230446A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH225257T 1938-07-02
CH230446T 1938-07-02

Publications (1)

Publication Number Publication Date
CH230446A true CH230446A (en) 1943-12-31

Family

ID=25726839

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230446D CH230446A (en) 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series.

Country Status (1)

Country Link
CH (1) CH230446A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9532938B2 (en) 2010-07-29 2017-01-03 Eastman Chemical Company Esters of O-substituted hydroxy carboxylic acids and preparations thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9532938B2 (en) 2010-07-29 2017-01-03 Eastman Chemical Company Esters of O-substituted hydroxy carboxylic acids and preparations thereof

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