CH226860A - Process for the preparation of an ethylene derivative. - Google Patents
Process for the preparation of an ethylene derivative.Info
- Publication number
- CH226860A CH226860A CH226860DA CH226860A CH 226860 A CH226860 A CH 226860A CH 226860D A CH226860D A CH 226860DA CH 226860 A CH226860 A CH 226860A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethylene
- preparation
- ethylene derivative
- ogyphenyl
- diethyl
- Prior art date
Links
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000005977 Ethylene Substances 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 phenol compound Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical group CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- MYWGVEGHKGKUMM-UHFFFAOYSA-N carbonic acid;ethene Chemical compound C=C.C=C.OC(O)=O MYWGVEGHKGKUMM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- 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 Herstellung eines Äthylenabkömmlings. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines A-thylen- abkömmlings, :das dadurch .gekennzeichnet ist, dass 1,2-Di-(p-ogyphenyl)-1,2-,diäthyl- äthylen mit Chlorkohlensäure-äthylester ver estert wird.
Der so erhaltene Bis-äthyl- kohlensäureester des 1,2-Di-(p-ogyphenyl)- 1,2-diäthyl-äthylens ist neu und schmilzt bei 118 . Es soll therapeutische Verwendung finden.
<I>Beispiel:</I> 18,4 g 1,2-Di-(p-ogyphenyl)-1,2-diäthyl- äthylen werden in 22,em' Pyridin unter Er wärmen gelöst. Bei 70 lässt man anschliessend 20 g Chlorkohlensäureäthylester unter Rüh ren zutropfen, so dass die Temperatur der Reaktionsmischung 70 nicht wesentlich über schreitet.
Die Mischung wird weitere zwei Stunden auf 70-75 erhitzt und ,dann in <B>300</B> cm' Eiswasser unter lebhaftem Rühren eingegossen. Nachdem Erstarren des ausge fallenen Produktes wird dieses abgesaugt und durch wiederholtes Waschen mit 2,5 öiger Salzsäure vom Pyridin befreit. Die Säure wird durch Nachwaschen mit Wasser ent fernt und das Reaktionsprodukt aus Alkohol umgelöst.
Nach gegebenenfalls wiederholtem Umkristallisieren schmilzt der entstandene Bis-äthylenkohlensäureester des 1,2-Di-(p- ogyphenyl)-1,2--diäthyl-äthylens bei 118 .
Statt in Pyridin kann man auch in wäss riger Lösung arbeiten und vom Natriumsalz der Phenolverbindung ausgehen, oder man kann entsprechend der Zugabe des Chlor- kohlensäureesters Natronlauge ,allmählich zur Reaktionsmischung zufügen.
Process for the preparation of an ethylene derivative. The subject of the present patent is a process for the production of an ethylene derivative: which is characterized by the fact that 1,2-di- (p-ogyphenyl) -1,2-, diethyl ethylene esterifies with ethyl chlorocarbonate becomes.
The bis-ethyl carbonic acid ester of 1,2-di- (p-ogyphenyl) -1,2-diethyl-ethylene thus obtained is new and melts at 118. It should find therapeutic use.
<I> Example: </I> 18.4 g of 1,2-di- (p-ogyphenyl) -1,2-diethyl-ethylene are dissolved in 22, em 'pyridine with heating. At 70, 20 g of ethyl chlorocarbonate are then added dropwise with stirring, so that the temperature of the reaction mixture does not significantly exceed 70.
The mixture is heated to 70-75 for a further two hours and then poured into 300 cm ice water with vigorous stirring. After the precipitated product has solidified, it is filtered off with suction and freed from the pyridine by repeated washing with 2.5% hydrochloric acid. The acid is removed by washing with water and the alcohol reaction product is redissolved.
After possibly repeated recrystallization, the resulting bis-ethylene carbonic acid ester of 1,2-di- (p-ogyphenyl) -1,2-diethylethylene melts at 118.
Instead of pyridine, it is also possible to work in aqueous solution and start from the sodium salt of the phenol compound, or caustic soda can be gradually added to the reaction mixture as the chlorocarbonic acid ester has been added.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE110239X | 1939-02-11 | ||
| CH213148T | 1940-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH226860A true CH226860A (en) | 1943-04-30 |
Family
ID=25725375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH226860D CH226860A (en) | 1939-02-11 | 1940-01-26 | Process for the preparation of an ethylene derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH226860A (en) |
-
1940
- 1940-01-26 CH CH226860D patent/CH226860A/en unknown
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