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
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
- C07C69/02—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
- 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
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of 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)
- 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)
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)
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 |
-
1938
- 1938-12-27 CH CH236169D patent/CH236169A/en unknown
Cited By (1)
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH236169A (en) | Process for the preparation of a new ester. | |
CH230446A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH234450A (en) | Process for the preparation of a p-nitrobenzoic acid ester. | |
DE720468C (en) | Process for the preparation of esters of ª ‡, ª ‡ -substituted 4, 4'-dioxy compounds of the stilbene series | |
AT212304B (en) | Process for the preparation of amino acid esters of threo-1- (p-nitrophenyl) -2-dichloroacetamidopropane-1,3-diols | |
CH223232A (en) | Process for the preparation of a new ester. | |
AT133143B (en) | Process for the preparation of readily soluble sodium salts of 4-oxy-3-acylaminobenzolaric acids (1) or their substitution products. | |
DE696404C (en) | Process for the preparation of a hexylresorcinol sulfonic acid | |
CH300418A (en) | Process for the preparation of a new thioether. | |
CH174281A (en) | Process for the preparation of acetyltropic acid-2,2-dimethyl-3-piperidyl-propanol ester. | |
CH121259A (en) | Process for the preparation of an acyl compound of amino-3-chloro-4-oxybenzene-1-arsic acid. | |
CH232836A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH230442A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH217885A (en) | Process for the preparation of a new ester. | |
CH230448A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH230445A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
CH230444A (en) | Process for the preparation of a new ester of the oxy-stilbene series. | |
CH204772A (en) | Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol. | |
CH205160A (en) | Method for producing a capillary-active connection. | |
CH206120A (en) | Process for the preparation of a new ester. | |
CH229076A (en) | Process for the manufacture of a medicament. | |
CH275687A (en) | Process for the preparation of a new benzoic acid ester. | |
CH179975A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
CH358434A (en) | Process for the preparation of salts of p-nitrophenyl-O-azidoacetyl-2-aminopropanediols |