CH223232A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH223232A CH223232A CH223232DA CH223232A CH 223232 A CH223232 A CH 223232A CH 223232D A CH223232D A CH 223232DA CH 223232 A CH223232 A CH 223232A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfuric acid
- acid ester
- parts
- ester
- water
- Prior art date
Links
Classifications
-
- 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
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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- 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
- C07C69/02—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Yeilahren zur Iierstellung eines neuen Esters. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Esters, welches dadurch gekennzeichnet ist, dass man a,ss-Diäthyl-a,ss-4,4'-dioxydiphenyl- äthan mit Sulfurierungsmitteln in den Di- schwefelsäureester überführt.
Als Sulfurierungsmittel eignet sich zum Beispiel Chlorsulfonsäure. Die Veresterung wird nach an sich bekannten Methoden vor genommen, wobei man zweckmässig Konden sationsmittel, wie z. B. Pyridin oder Chino- lin, verwendet.
Der so erhaltene Sehwefelsäureester bildet ein weisses Pulver. Seine Alkalisalze sind in Wasser leicht löslich. Die neue Verbindung hat eine Wirkung im Oestrus- und Uterus wachstumstest. Sie soll therapeutische Ver wendung finden.
<I>Beispiel:</I> Eine Lösung von 1 Teil a,ss-Diäthyl-a,ss- 4,4'-dioxydiphenyläthan in 5 Teilen Pyridin wird tropfenweise zu einer stark gekühlten Lösung von 2 Teilen Chlorsulfonsäure in 5 Teilen Pyridin gegeben. Die Mischung er starrt bald zu einem Kristallbrei. Man lässt eine Viertelstunde im Eis und darnach eine Stunde bei Zimmertemperatur stehen. Hier auf giesst man die Reaktionsmasse in über schüssige gesättigte Natriumbicarbonatlösung. Unverbrauchtes Ausgangsmaterial wird durch Ausschütteln mit Äther entfernt.
Die wäs serige Lösung versetzt man dann mit 211- Salzsäure und fällt den Sehwefelsäureester des a,ss-Diäthyl-a,ss-4,4'-dioxydiphenyl-äthan als weisses voluminöses Pulver aus. Durch Umkristallisieren oder Umfällen lässt sich die ser Ester weiter reinigen.
Wird 1 Teil des Endproduktes des bean spruchten Verfahrens in 20 Teilen Wasser gelöst und mit einer Lösung von 3 Teilen Cal ciumacetat in 10 Teilen Wasser versetzt, so fällt das Calciumsalz des a,ss-Diäthyl-a,ss-4,4'- dioxydiphenyl-äthan-schwefelsäureesters als weisses Pulver aus.
Werden 4,28 Teile des oben beschriebenen Schwefelsäureesters in 20 Teilen Wasser ge- löst, mit 0,80 Teilen Natriumhydroxyd in 5 Teilen Wasser versetzt, und die Lösung im Vakuum zur Trockne verdampft, so erhält man als Rückstand das wasserlösliche Na triumsalz des oben erwähnten Schwefelsäure- esters, welches durch Umkristallisieren weiter gereinigt werden kann.
Years to make a new ester. The subject matter of the present patent is a process for the preparation of a new ester, which is characterized in that α, β-diethyl-α, β-4,4'-dioxydiphenylethane is converted into the di-sulfuric acid ester with sulfurizing agents.
A suitable sulfurizing agent is, for example, chlorosulfonic acid. The esterification is carried out according to methods known per se, using appropriate condensation agents such. B. pyridine or quinoline used.
The sulfuric acid ester obtained in this way forms a white powder. Its alkali salts are easily soluble in water. The new compound has an effect in the oestrus and uterus growth test. It should find therapeutic use.
<I> Example: </I> A solution of 1 part of a, ss-diethyl-a, ss- 4,4'-dioxydiphenylethane in 5 parts of pyridine is added dropwise to a strongly cooled solution of 2 parts of chlorosulfonic acid in 5 parts of pyridine . The mixture he soon stares into a slurry of crystals. It is left to stand in the ice for a quarter of an hour and then for an hour at room temperature. Here, the reaction mass is poured into excess saturated sodium bicarbonate solution. Unused starting material is removed by shaking with ether.
The aqueous solution is then mixed with 211 hydrochloric acid and the sulfuric acid ester of a, ß-diethyl-α, ß-4,4'-dioxydiphenyl-ethane precipitates as a white voluminous powder. This ester can be further purified by recrystallization or reprecipitation.
If 1 part of the end product of the claimed process is dissolved in 20 parts of water and a solution of 3 parts of calcium acetate in 10 parts of water is added, the calcium salt of α, β-diethyl-α, β-4,4'-dioxydiphenyl falls -ethane-sulfuric acid ester as a white powder.
If 4.28 parts of the sulfuric acid ester described above are dissolved in 20 parts of water, 0.80 parts of sodium hydroxide in 5 parts of water are added, and the solution is evaporated to dryness in vacuo, the residue obtained is the water-soluble sodium salt of the above-mentioned Sulfuric acid ester, which can be further purified by recrystallization.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH217885T | 1938-12-27 | ||
| CH223232T | 1939-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH223232A true CH223232A (en) | 1942-08-31 |
Family
ID=25726078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH223232D CH223232A (en) | 1938-12-27 | 1939-06-01 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH223232A (en) |
-
1939
- 1939-06-01 CH CH223232D patent/CH223232A/en unknown
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