CH225257A - 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
CH225257A
CH225257A CH225257DA CH225257A CH 225257 A CH225257 A CH 225257A CH 225257D A CH225257D A CH 225257DA CH 225257 A CH225257 A CH 225257A
Authority
CH
Switzerland
Prior art keywords
preparation
oxy
new ester
dioxystilbene
diethyl
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 CH225257A publication Critical patent/CH225257A/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

  

  Verfahren zur Darstellung eines neuen Esters der     Ogy-stilbenreihe.       Es     wurde    gefunden, dass man zu einem  neuen Ester gelangen kann, wenn man     a,a'-          Diäthyl-4,4'-dioxystilben    mit einem     pro-          pionylierenden    Mittel     behandelt.     



  Geeignete     propionylierende    Mittel sind  zum Beispiel die     Propionsäure    selbst, ihre       Halogenide    oder Ester mit niederen Alko  holen     (Umesterung),    ihr     Anhydrid    sowie  auch das von ihr abgeleitete     Keten.     



  Die neue Verbindung, das     a,ä        -Diäthyl-          4,4'-dioxystilben-dipropionat,    schmilzt bei  106-107  . Sie zeigt gegenüber den bekann  ten hormonal wirksamen Verbindungen ohne       Steroid-Charakter    eine     protrahiertere    Wir  kung im     Oestrus-    und     Uteruswachstumstest     und soll deshalb therapeutische Verwendung  finden.  



  <I>Beispiel:</I>  1 Teil     a,a'-Diäthyl-4,4'-dioxystilben    wird  in 15 Teilen     Pyridin    und 4 Teilen     Propion-          säureanhydrid    einige Zeit auf 105   erhitzt.    Nach dem Erkalten verdünnt man langsam  mit 200 Teilen Wasser. Das ausfallende 01       wird    in Äther aufgenommen und mit       n-Schwefelsäure,    Wasser und n/10 Natron  lauge gewaschen. Nach     Abdestillieren    des  Äthers erhält man den     Dipropionsäureester,     der sich durch     Umkristallisieren    aus verdünn  tem Methanol reinigen lässt. F. 106-107  .



  Process for the preparation of a new ester of the Ogy stilbene series. It has been found that a new ester can be obtained if a, a'-diethyl-4,4'-dioxystilbene is treated with a propionylating agent.



  Suitable propionylating agents are, for example, propionic acid itself, its halides or esters with lower alcohols (transesterification), its anhydride and also the ketene derived from it.



  The new compound, the a, ä -diethyl 4,4'-dioxystilbene dipropionate, melts at 106-107. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterine growth test and should therefore be used therapeutically.



  <I> Example: </I> 1 part of a, a'-diethyl-4,4'-dioxystilbene in 15 parts of pyridine and 4 parts of propionic anhydride is heated to 105 for some time. After cooling, it is slowly diluted with 200 parts of water. The precipitated 01 is taken up in ether and washed with n-sulfuric acid, water and n / 10 sodium hydroxide solution. After distilling off the ether, the dipropionic acid ester is obtained, which can be purified by recrystallization from dilute methanol. F. 106-107.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man a,ä -Diäthyl-4,4'-dioxystilben mit einem pro pionylierenden Mittel behandelt. Die neue Verbindung, das a,a'-Diäthyl- 4,4'-dioxystilben-dipropionat, schmilzt bei l06-107 . Sie zeigt gegenüber den bekann ten hormonal wirksamen Verbindungen ohne Steroid-Charakter eine protrahiertere Wirkung im Oestrus- und Uteruswachstumstest und soll deshalb therapeutische Verwendung finden. PATENT CLAIM: Process for the preparation of a new ester, characterized in that a, ä -diethyl-4,4'-dioxystilbene is treated with a propionylating agent. The new compound, the a, a'-diethyl 4,4'-dioxystilbene dipropionate, melts at 106-107. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterine growth test and should therefore be used therapeutically. UNTERANSPRüCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als propionylie- rendes Mittel Propionsäureanhy drid verwen det wird. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als propionylie- rendes Mittel ein Propionsäurehalogenid ver wendet wird. SUBClaims: 1. Method according to claim, characterized in that propionic anhydride is used as the propionylating agent. 2. The method according to claim, characterized in that a propionic acid halide is used as the propionylating agent.
CH225257D 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series. CH225257A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH225257A true CH225257A (en) 1943-01-15

Family

ID=4453947

Family Applications (1)

Application Number Title Priority Date Filing Date
CH225257D CH225257A (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) CH225257A (en)

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