CH236169A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH236169A
CH236169A CH236169DA CH236169A CH 236169 A CH236169 A CH 236169A CH 236169D A CH236169D A CH 236169DA CH 236169 A CH236169 A CH 236169A
Authority
CH
Switzerland
Prior art keywords
sep
diethyl
preparation
new
ester
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 CH236169A publication Critical patent/CH236169A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22Esters 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
    • C07C69/28Esters 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205Compounds 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
    • C07C39/21Compounds 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
    • C07C39/215Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12Acetic acid esters
    • C07C69/16Acetic acid esters of dihydroxylic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96Esters of carbonic or haloformic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Steroid Compounds (AREA)

Description

  

      Terfahren    zur Darstellung eines neuen Esters.    Es wurde gefunden,     da-ss    man zu einem  neuen Ester gelangen kann, wenn     mann          a,ss-Diäthyl-a,ss--di-(p-ogyphenyl)-äthan    der  Formel  
EMI0001.0005     
    mit einem     Veresterungsmittel    behandelt, das  den     Athylkohlensäurerest    einzuführen vermag.  



  Als     Veresterungsmittel    eignet sich z. B.       Chlo.rkohlensäureäthylester.     Die neue Verbindung, der     a,ss-Diäthyl-.     



       a,ss-di-   <I>(p</I> -     ogyphenyl)        -äthan-,di-;äthylko#hlen-          säureester,    bildet farblose Kristalle vom  F. 15ss-154 . Sie zeigt gegenüber den be  kannten hormonal wirksamen     Verbindungen     ohne     Steroid-Charakter    eine     protrahiertere       Wirkung im     Ostrun-    und     Uterus-Wachstums-          test    und soll deshalb therapeutische Verwen  dung finden.  



  <I>Beispiel:</I>  Zu einem in Eis .gekühlten Gemisch von  1 Teil     a,ss-Diäthyl-a,ss-di-(p-ogyphenyl)-äthan     in 2 Teilen     Pyridin    werden tropfenweise und  unter     Rühren    2 Teile     ChlorameisensäuTe-          ä.thylester    gegeben. Die     entstandene        .gelbe     Mischung     wird    im Wasserbad bis zur Ent  färbung     mässig    erwärmt und darauf einige  Stunden bei Zimmertemperatur     stehen    ge  lassen.

   Der entstandene     Kristallbrei        wird     dann in Wasser und Äther aufgenommen und  die ätherische Lösung     nacheinander    mit ver  dünnter Schwefelsäure,     Wasser,        verdünnter     Natronlauge und nochmals mit Wasser ge  waschen. Nach dem Trocknen und Verdamp  fen der ätherischen Lösung erhält man den       Di-äthylkohlensäureester    des     a,ss-Diäthyl-          a,ss-d.i-(p-ogyphenyl)-äthans    als     weissen    kri  stallinischen     Rückstand.    Aus     Äthanol    um  gelöst schmilzt er bei 15ss-154 .



      Driving to the representation of a new ester. It has been found that a new ester can be obtained if a, ss-diethyl-a, ss-di- (p-ogyphenyl) -ethane of the formula
EMI0001.0005
    treated with an esterifying agent capable of introducing the ethyl carbonic acid residue.



  Suitable esterifying agents are, for. B. Chlo.rkohlensäureäthylester. The new compound, the a, ss-diethyl.



       a, ss-di- <I> (p </I> - ogyphenyl) -ethane, di-; ethyl carbonate, forms colorless crystals of F. 15ss-154. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the ostrum and uterus growth test and should therefore find therapeutic use.



  <I> Example: </I> To a mixture, cooled in ice, of 1 part of a, ss-diethyl-a, ss-di- (p-ogyphenyl) -ethane in 2 parts of pyridine, 2 parts of chloroformic acid are added dropwise and with stirring - given ethyl ester. The resulting yellow mixture is heated moderately in a water bath until discoloration and then left to stand for a few hours at room temperature.

   The resulting crystal pulp is then absorbed in water and ether and the ethereal solution is washed successively with dilute sulfuric acid, water, dilute sodium hydroxide solution and again with water. After drying and evaporation of the ethereal solution, the diethyl carbonate of a, ss-diethyl a, ss-d.i- (p-ogyphenyl) ethane is obtained as a white crystalline residue. Dissolved from ethanol it melts at 15ss-154.

 

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung eine;, neuen Esters, dadurch gekennzeichnet, dass man a,ss-Diäthyl-a,ss-,di-(p-oxyphenyl)-äthan der Formel EMI0002.0005 mit einem Veresterungsmittel behandelt, das denÄthylkohlensäurere,st einzufiihren vermag. <B> PATENT CLAIM: </B> Process for the preparation of a ;, new ester, characterized in that a, ss-diethyl-a, ss-, di- (p-oxyphenyl) -ethane of the formula EMI0002.0005 treated with an esterifying agent capable of introducing the ethyl carbonic acid. EMI0002.0009 Die <SEP> neue <SEP> Verbindung, <SEP> der <SEP> a,ss-Diäthyl a,l- <SEP> di <SEP> - <SEP> (p <SEP> - <SEP> oxyphenyl) <SEP> - <SEP> ä.than <SEP> -di-äthylkohlen säureester. <SEP> bildet <SEP> farblose <SEP> Kristalle <SEP> vom <tb> F. <SEP> 1;5i3-1,54". <SEP> Sie <SEP> zeigt <SEP> gegenüber <SEP> den <SEP> be kannten <SEP> hormonal <SEP> wirksamen <SEP> Verbindungen <tb> ohne <SEP> Steroid-Charakter <SEP> eine <SEP> protrahiertere <tb> Wirkuri- <SEP> im <SEP> Ostriv-:- <SEP> und <SEP> U <SEP> terus--N##@@achstums test <SEP> und <SEP> soll <SEP> deshalb <SEP> therapeutische <SEP> Verwen dung <SEP> finden. <tb> UN <SEP> TERANSPRUCII <tb> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeichnet, <SEP> dass <SEP> als <SEP> Veresterungsmittel <tb> Chlora.m.eisensä.ureiithvlester <SEP> verwendet <SEP> wird. EMI0002.0009 The <SEP> new <SEP> compound, <SEP> der <SEP> a, ss-diethyl a, l- <SEP> di <SEP> - <SEP> (p <SEP> - <SEP> oxyphenyl) <SEP > - <SEP> Ä.than <SEP> -di-ethyl carbonic acid ester. <SEP> forms <SEP> colorless <SEP> crystals <SEP> from <tb> F. <SEP> 1; 5i3-1.54 ". <SEP> You <SEP> shows <SEP> compared to <SEP> the <SEP> known <SEP> hormonally <SEP> effective <SEP> compounds <tb> without <SEP> steroid character <SEP> a <SEP> more protracted <tb> Wirkuri- <SEP> in the <SEP> Ostriv -: - <SEP> and <SEP> U <SEP> terus - N ## @@ achstums test <SEP> and <SEP> should <SEP> therefore < SEP> find therapeutic <SEP> use <SEP>. <tb> UN <SEP> TERANSPRUCII <tb> Method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> that <SEP> as <SEP> esterifying agent <tb> Chlora.m.eisenä.ureiithvlester <SEP> is used <SEP> is used.
CH236169D 1938-12-27 1938-12-27 Process for the preparation of a new ester. CH236169A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH217885T 1938-12-27
CH236169T 1938-12-27

Publications (1)

Publication Number Publication Date
CH236169A true CH236169A (en) 1945-01-15

Family

ID=25726081

Family Applications (1)

Application Number Title Priority Date Filing Date
CH236169D CH236169A (en) 1938-12-27 1938-12-27 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH236169A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094994A (en) * 1976-12-22 1978-06-13 Klinge Pharma Gmbh Novel di-(3'-hydroxyphenyl)-alkane compounds, process of preparation and their use in medicine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094994A (en) * 1976-12-22 1978-06-13 Klinge Pharma Gmbh Novel di-(3'-hydroxyphenyl)-alkane compounds, process of preparation and their use in medicine

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