CH299532A - Process for the preparation of a substituted cumalic acid ester. - Google Patents
Process for the preparation of a substituted cumalic acid ester.Info
- Publication number
- CH299532A CH299532A CH299532DA CH299532A CH 299532 A CH299532 A CH 299532A CH 299532D A CH299532D A CH 299532DA CH 299532 A CH299532 A CH 299532A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid ester
- substituted
- preparation
- cumalic
- cumalic acid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines substituierten Cumalinsäureesters. Es wurde gefunden, dass in 4- und 6-Stel- Lung durch Alkylreste substituierte Cumalin- säuren bzw. deren Ester bemerkenswerte anti bakterielle Wirksamkeit aufweisen.
Insbeson dere haben sich solche Cumalinsäuren oder deren Ester ausgezeichnet, die in 4-Stellung durch die Methylgruppe und in 6-Stellung durch einen geradkettigen, verzweigten, ge sättigten oder ungesättigten Alkylrest mit mehr als einem C-Atom substituiert sind.
Die neuen Verbindungen werden zweck mässig durch Einwirkung von ss-Chlor-iso- erotonsäureester auf Alkaliverbindungen von Homologen des Acetessigesters dargestellt. Die Umsetzung wird vorteilhaft in einem inerten Lösungsmittel, wie beispielsweise Äther, Ben zol oder Toluol, und bei erhöhter Temperatur durchgeführt. Die substituierten Cumalin- säuren fallen in Form ihrer Ester an.
Diese können durch fraktionierte Destillation ge reinigt und gegebenenfalls in an sich bekann ter Weise durch Erwärmen mit verdünntem Alkali zu den entsprechenden Säuren verseift werden.
Gegenstand des Patentes ist nun ein Ver fahren zur Herstellung von 4-Methyl-6-hexyl- cumalinsäureäthylester, das dadurch gekenn zeichnet ist, dass man einen ss-Chlor-isocroton- säureester der Formel CH3-CCl=CH-COOR', wobei R' einen niederen Alkylrest darstellt, mit einer Alkaliverbindung des Oenantyl- essi;säureäthylesters -umsetzt. <I>Beispiel:
</I> 16 Gewichtsteile Oenantyl-essigsäureäthyl- ester werden in 100 Raumteilen absolutem Benzol mit 2 Gewichtsteilen Natrium versetzt und nach erfolgter Bildung des Natriumsalzes mit 11 Gewichtsteilen- ss-Chlor-isocrotonsäure- äthylester versetzt. Man kocht 48 Stunden am Rückflitss und destilliert das Benzol bei Atmo sphärendruck ab.
Der Rückstand wird im Vakuum bei 0,03 mm destilliert. Das bei 115 bis 125 C übergehende gelbe Öl stellt reinen 4-Methyl-6-hexyl-cumalinsäitreäthylester dar.
Die neue Verbindung soll als Desinfek tionsmittel und als Heilmittel Verwendung finden.
Process for the preparation of a substituted cumalic acid ester. It has been found that cumalic acids or their esters substituted by alkyl radicals in the 4- and 6-position have remarkable antibacterial activity.
In particular, those cumalic acids or their esters have distinguished themselves which are substituted in the 4-position by the methyl group and in the 6-position by a straight-chain, branched, saturated or unsaturated alkyl radical with more than one carbon atom.
The new compounds are expediently prepared by the action of ß-chloro-iso-erotonic acid ester on alkali compounds of homologues of the acetoacetic ester. The reaction is advantageously carried out in an inert solvent, such as, for example, ether, benzene or toluene, and at an elevated temperature. The substituted cumalic acids are obtained in the form of their esters.
These can be purified by fractional distillation and, if necessary, saponified in a manner known per se by heating with dilute alkali to give the corresponding acids.
The subject of the patent is now a process for the production of 4-methyl-6-hexyl-cumalinsäureäthylester, which is characterized in that one ss-chloro-isocrotonic acid ester of the formula CH3-CCl = CH-COOR ', where R 'represents a lower alkyl radical, reacted with an alkali metal compound of the oenantyl ethyl ester. <I> example:
16 parts by weight of ethyl oenantyl acetic acid are added to 100 parts by volume of absolute benzene with 2 parts by weight of sodium and, after the formation of the sodium salt, 11 parts by weight of ß-chloro-isocrotonic acid ethyl ester are added. It is refluxed for 48 hours and the benzene is distilled off at atmospheric pressure.
The residue is distilled in vacuo at 0.03 mm. The yellow oil passing over at 115 to 125 C is pure ethyl 4-methyl-6-hexyl-cumalinate.
The new compound is to be used as a disinfectant and as a remedy.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH299532T | 1951-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH299532A true CH299532A (en) | 1954-06-15 |
Family
ID=4490348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH299532D CH299532A (en) | 1951-10-19 | 1951-10-19 | Process for the preparation of a substituted cumalic acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH299532A (en) |
-
1951
- 1951-10-19 CH CH299532D patent/CH299532A/en unknown
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