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
Links
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)
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)
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 |
-
1938
- 1938-07-02 CH CH230446D patent/CH230446A/en unknown
Cited By (1)
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH230446A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH236169A (en) | Process for the preparation of a new ester. | |
DE861839C (en) | Process for the preparation of threo-1- (4'-nitrophenyl) -2-dichloroacetylamino-1, 3-dichloropropane | |
DE695387C (en) | Process for the production of water- or lipoid-soluble salts with locally anesthetically effective, optionally amino-substituted benzoic acid alkyl or alkamine esters | |
DE674516C (en) | Process for the production of a water-soluble, solid mixture of alkali silicates and alkali acetates | |
AT210563B (en) | Process for the production of a new therapeutically valuable calcium salt | |
AT142027B (en) | Process for the preparation of acyl derivatives of the dihydrofollicle hormone. | |
DE689765C (en) | Process for the production of dry, non-hygroscopic double salts from calcium lactate and calcium chloride | |
CH230445A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH230444A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH90587A (en) | Process for the preparation of benzyl p-aminobenzoate. | |
CH230442A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
DE619342C (en) | Process for the production of aqueous suspensions or emulsions | |
AT143480B (en) | Process for the preparation of a quinine compound. | |
CH169243A (en) | Process for the preparation of 5-chloro-2-benzoyl-acetylamino-1-methoxybenzene-3-sulfonic acid. | |
CH217885A (en) | Process for the preparation of a new ester. | |
CH230980A (en) | Process for the preparation of B- (p-oxyphenyl) -isopropyl-ethylamine. | |
CH230443A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH230440A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH230441A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH223232A (en) | Process for the preparation of a new ester. | |
CH206625A (en) | Process for preparing a sulfonic acid amide compound. | |
CH300255A (en) | Process for the production of an intermediate product. | |
CH91107A (en) | Process for the preparation of a dioxynaphtoylbenzoic acid ester. | |
CH234450A (en) | Process for the preparation of a p-nitrobenzoic acid ester. |