CH300714A - 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
- CH300714A CH300714A CH300714DA CH300714A CH 300714 A CH300714 A CH 300714A CH 300714D A CH300714D A CH 300714DA CH 300714 A CH300714 A CH 300714A
- Authority
- CH
- Switzerland
- Prior art keywords
- substituted
- preparation
- acid ester
- water
- ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 cumalic acid ester Chemical class 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- UKRVECBFDMVBPU-UHFFFAOYSA-N ethyl 3-oxoheptanoate Chemical compound CCCCC(=O)CC(=O)OCC UKRVECBFDMVBPU-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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 Cumalinsänreesters. Es wurde gefunden, dass Cumalinsäuren und deren Ester, die in 4- und 6-Stellung durch einen Alkylrest substituiert sind, ins besondere solche, bei denen die Alkylreste mehr als ein C-Atom aufweisen, bemerkens werte antibakterielle Wirkung zeigen.
So ver mag die 4,6-Dibutylcumalinsäure das Wachs tum von Mycobacterium Plilei in syntheti schem Milieu noch in einer Verdünnung von 15 y pro cmj zu 90-% und dasjenige von Sta- phylococcus aureus zu 65 % zu hemmen. Die neuen Verbindungen sollen als Arzneimittel verwendet werden.
Die neuen Verbindungen können in an sich bekannter Weise durch Kondensation der Homologen des Acetessigesters unter dem Ein fluss von hochkonzentrierten, vorzug@veise was serfreien Mineralsäuren, insbesondere Salz säure oder Schwefelsäure, erhalten werden. Die Kondensation mit Schwefelsäure führt zu einem Gemisch von freier Säure und Ester, das durch fraktionierte Destillation im Hochvakuum getrennt werden kann.
Gegenstand des Patentes ist nun ein Ver fahren zur Herstellung von 4,6-Dibutyl-euma- linsäitreäthylester, das dadurch gekennzeich net ist, dass man auf Valeryl-essigsäureäthyl- ester bei gewöhnlicher Temperatur eine hoch konzentrierte Mineralsäure einwirken lässt, das Reaktionsprodukt mit Wasser verdünnt, die wässerige Lösung mit einem mit Wasser nicht misehbaren Lösungsmittel extrahiert und aus dem Extrakt den Ester isoliert.
<I>Beispiel:</I> 10 Gewichtsteile Valeryl-essigsäureäthyl- ester werden mit 25 Gewichtsteilen konzen trierter Schwefelsäure versetzt und das Ge misch 10 Tage bei Zimmertemperatur aufbe wahrt.
Hernach wird die Lösung in Wasser gegossen und mit Äther ausgeschüttelt. Der aus der Ätherlösung nach Trocknen und Ab dampfen des Äthers erhaltene 4,6-Dibutyl- camalinsäureäthylester destilliert unter einem Druck von 0,05 mm bei 144-146 C und stellt ein gelbes Öl dar:
Als zweite Fraktion vom Siedepunkt C' mm 150 C erhält man ein gelbes Öl, -das beim Erkalten halbfest wird und die 4,6-Di- butyl-cumalinsäure darstellt.
Process for the preparation of a substituted cumalinic acid ester. It has been found that cumalic acids and their esters which are substituted in the 4- and 6-positions by an alkyl radical, in particular those in which the alkyl radicals have more than one carbon atom, show a remarkable antibacterial effect.
Thus, 4,6-dibutylcumalic acid is able to inhibit the growth of Mycobacterium Plilei in a synthetic medium even at a dilution of 15% per cm1 and that of Staphylococcus aureus to 65%. The new compounds are intended to be used as drugs.
The new compounds can be obtained in a manner known per se by condensation of the homologues of the acetoacetic ester under the influence of highly concentrated, preferably water-free mineral acids, in particular hydrochloric acid or sulfuric acid. The condensation with sulfuric acid leads to a mixture of free acid and ester, which can be separated by fractional distillation in a high vacuum.
The subject of the patent is now a process for the production of 4,6-dibutyl-eumalinsäitreäthylester, which is characterized in that a highly concentrated mineral acid is allowed to act on valeryl-acetic acid ethyl ester at ordinary temperature and the reaction product is diluted with water , the aqueous solution is extracted with a solvent that cannot be measured with water and the ester is isolated from the extract.
<I> Example: </I> 10 parts by weight of ethyl valeryl acetate are mixed with 25 parts by weight of concentrated sulfuric acid and the mixture is kept for 10 days at room temperature.
Then the solution is poured into water and shaken out with ether. The ethyl 4,6-dibutyl camalinate obtained from the ether solution after drying and evaporation of the ether is distilled under a pressure of 0.05 mm at 144-146 C and is a yellow oil:
A yellow oil is obtained as the second fraction with a boiling point of C mm 150 C, which becomes semi-solid on cooling and represents 4,6-di-butyl-cumalic acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH300714T | 1951-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300714A true CH300714A (en) | 1954-08-15 |
Family
ID=4490811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300714D CH300714A (en) | 1951-10-18 | 1951-10-18 | Process for the preparation of a substituted cumalic acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300714A (en) |
-
1951
- 1951-10-18 CH CH300714D patent/CH300714A/en unknown
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