CH261123A - Process for the preparation of a naphthylpropionic acid. - Google Patents
Process for the preparation of a naphthylpropionic acid.Info
- Publication number
- CH261123A CH261123A CH261123DA CH261123A CH 261123 A CH261123 A CH 261123A CH 261123D A CH261123D A CH 261123DA CH 261123 A CH261123 A CH 261123A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid
- parts
- naphthyl
- ether
- Prior art date
Links
- VKCNNDPZFOVURD-UHFFFAOYSA-N 2-naphthalen-1-ylpropanoic acid Chemical compound C1=CC=C2C(C(C(O)=O)C)=CC=CC2=C1 VKCNNDPZFOVURD-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- -1 propyl halide Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PQUSVJVVRXWKDG-UHFFFAOYSA-N methyl 2-bromo-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Br PQUSVJVVRXWKDG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung einer Naphthylpropionsäure. Es wurde gefunden, dass man zu einer Naphthylpropionsäure gelangen kann, wenn man ein a-(6-Methoxy-naphthyl-2)-propyl- halogenid mit einem a-Halogen-isobuttersäure- ester in Gegenwart eines halogenabspaltenden Mittels umsetzt und im erhaltenen Produkt die veresterte Carboxylgruppe verseift.
Das bekannte Endprodukt des Verfahrens, die ss-(6-Methoxy-naphthyl-2)-,l-äthyl-a,a-di- methyl-propionsäure vom Schmelzpunkt 131 bis 133 , ist oestrogen wirksam. Es soll thera peutische Verwendung finden oder als Zwi schenprodukt zur Herstellung therapeutisch verwendbarer Verbindungen dienen.
Als halogenabspaltende Mittel verwendet man z. B. Metalle oder Metallegierungen, z. B. Zink, Magnesium, Natrium und dergleichen in Gegenwart von Verdünnungsmitteln, wie Äther, Benzol, Toluol und dergleichen. Die Verseifung der veresterten Carboxylgruppe kann in an sieh bekannter Weise durchgeführt werden.
<I>Beispiel:</I> 11 Gewichtsteile a-(6-Methoxy-naphthyl- 2)-propylehlorid der Formel
EMI0001.0017
werden in 200 Volumteilen Äther gelöst, mit 9 Volumteilen a-Brom-isobuttersäuremethyl- ester vermischt und in .eine Suspension von 10 Gewichtsteilen Zinkflitter in 100 Volum- teilen Äther getropft, wobei bald Reaktion eintritt. Zur Beendigung derselben kocht man noch 1/2 Stunde, kühlt ab, giesst auf Eis und extrahiert das Reaktionsprodukt mit Äther.
Der Ätherrückstand wird ohne weitere Reini gung zwecks Hydrolyse der Carbomethoxy- gruppe in einer Mischung von 10 Gewichts teilen Kaliumhydroxyd und 50 Volumteilen Äthylalkohol im offenen Gefäss auf etwa 160 erhitzt und die gebildete Säure in üblicher Weise isoliert. Die so erhaltene ,B-(6-Methoxy- naphthyl-2) -ss-äthyl-a,a-dimethyl-propionsäure der Formel
EMI0001.0030
schmilzt nach Umlösen aus verdünntem Me thanol bei 131 bis 133 .
Process for the preparation of a naphthylpropionic acid. It has been found that a naphthylpropionic acid can be obtained if an α- (6-methoxy-naphthyl-2) -propyl halide is reacted with an α-halo-isobutyric acid ester in the presence of a halogen-releasing agent and in the product obtained esterified carboxyl group saponified.
The known end product of the process, ss- (6-methoxy-naphthyl-2) -, l-ethyl-a, a-dimethylpropionic acid with a melting point of 131 to 133, is estrogenically active. It should find therapeutic use or serve as an inter mediate product for the preparation of therapeutically useful compounds.
As halogen-releasing agents are used, for. B. metals or metal alloys, e.g. B. zinc, magnesium, sodium and the like in the presence of diluents such as ether, benzene, toluene and the like. The saponification of the esterified carboxyl group can be carried out in a manner known per se.
<I> Example: </I> 11 parts by weight of a- (6-methoxy-naphthyl-2) -propyl chloride of the formula
EMI0001.0017
are dissolved in 200 parts by volume of ether, mixed with 9 parts by volume of methyl α-bromo-isobutyrate and added dropwise to a suspension of 10 parts by weight of zinc flakes in 100 parts by volume of ether, with reaction soon occurring. To end the same, boil for another 1/2 hour, cool, pour onto ice and extract the reaction product with ether.
The ether residue is heated to about 160 in an open vessel for hydrolysis of the carbomethoxy group in a mixture of 10 parts by weight of potassium hydroxide and 50 parts by volume of ethyl alcohol and the acid formed is isolated in the usual way. The B- (6-methoxynaphthyl-2) -ss-ethyl-a, a-dimethyl-propionic acid of the formula obtained in this way
EMI0001.0030
Melts at 131 to 133 after dissolving from dilute methanol.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261123T | 1947-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261123A true CH261123A (en) | 1949-04-30 |
Family
ID=4473810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261123D CH261123A (en) | 1947-07-11 | 1947-07-11 | Process for the preparation of a naphthylpropionic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261123A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6608111B1 (en) | 1998-06-23 | 2003-08-19 | Southern Illinois University Office Of Research, Development And Administration | Method for treating or preventing prostatic conditions |
-
1947
- 1947-07-11 CH CH261123D patent/CH261123A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6608111B1 (en) | 1998-06-23 | 2003-08-19 | Southern Illinois University Office Of Research, Development And Administration | Method for treating or preventing prostatic conditions |
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