CH217885A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH217885A CH217885A CH217885DA CH217885A CH 217885 A CH217885 A CH 217885A CH 217885D A CH217885D A CH 217885DA CH 217885 A CH217885 A CH 217885A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- oxyphenyl
- hexadiene
- new ester
- propionylating agent
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 230000012173 estrus Effects 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- -1 propionic acid halide Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines neuen Esters. Es wurde gefunden, dass man zu einem neuen Ester gelangen kann, wenn man 3,4 Di-(p-oxyphenyl)-hexadien-(2,4) der Formel:
EMI0001.0001
mit einem Propionylierungsmittel behandelt. Geeignete propionylierende Mittel sind zum Beisipel die Propionsäure selbst, ihre Halogenide oder Ester mit niederen Alko holen (Umesterung), ihr Anhydrid sowie auch das von ihr abgeleitete Beten.
Die neue Verbindung, das 3,4-Di-(p-oxy- phenyl) - hexadien - (2,4) - dipropionat bildet farblose Kristalle. Es zeigt gegenüber den bekannten hormonal wirksamen Verbindungen ohne Steroid-Charakter eine protrahiertere Wirkung im Oestrus- und Uteruswachstums- test und soll deshalb therapeutische Verwen dung finden.
<I>Beispiel:</I> 1 Teil 3,4-Di-(p-oxyphenyl)-hexadien-(2,4) wird in 15 Teilen Pyridin und 5 Teilen Pro- pionsäureanhydrid einige Zeit auf 110 er hitzt. Hierauf lässt man erkalten und ver setzt das Gemisch mit Wasser, wobei sich ein Öl ausscheidet. Dieses wird in Äther auf genommen und nacheinander mit n-Schwefel- säure, Wasser und n/10-Natronlauge ge waschen. Nach dem Verdunsten des Äthers erhält man das Dipropionat. Es wird aus wässerigen Äthanol umgelöst, bis sich farb lose Kristalle ergeben.
Process for the preparation of a new ester. It has been found that a new ester can be obtained if 3,4 di- (p-oxyphenyl) -hexadiene- (2,4) of the formula:
EMI0001.0001
treated with a propionylating agent. Suitable propionylating agents are, for example, the propionic acid itself, its halides or esters with lower alcohols (transesterification), its anhydride and also the praying derived from it.
The new compound, 3,4-di- (p-oxyphenyl) hexadiene (2,4) dipropionate, forms colorless crystals. 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 find therapeutic use.
<I> Example: </I> 1 part of 3,4-di- (p-oxyphenyl) -hexadiene- (2,4) in 15 parts of pyridine and 5 parts of propionic anhydride is heated to 110 for some time. The mixture is then left to cool and water is added, an oil separating out. This is taken up in ether and washed successively with n-sulfuric acid, water and n / 10 sodium hydroxide solution. Dipropionate is obtained after the ether has evaporated. It is redissolved from aqueous ethanol until colorless crystals result.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH217885T | 1938-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217885A true CH217885A (en) | 1941-11-15 |
Family
ID=4450354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217885D CH217885A (en) | 1938-12-27 | 1938-07-21 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217885A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500856A (en) * | 1946-12-17 | 1950-03-14 | Reed & Carnrick | Aliphatic esters of 3, 4-bis-(mu-methyl-p-hydroxyphenyl)-2, 4-hexadiene |
-
1938
- 1938-07-21 CH CH217885D patent/CH217885A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500856A (en) * | 1946-12-17 | 1950-03-14 | Reed & Carnrick | Aliphatic esters of 3, 4-bis-(mu-methyl-p-hydroxyphenyl)-2, 4-hexadiene |
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