CH296481A - Process for the production of a pyran derivative. - Google Patents
Process for the production of a pyran derivative.Info
- Publication number
- CH296481A CH296481A CH296481DA CH296481A CH 296481 A CH296481 A CH 296481A CH 296481D A CH296481D A CH 296481DA CH 296481 A CH296481 A CH 296481A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- capronyl
- production
- pyran derivative
- basic catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- -1 unsaturated alkyl radical Chemical class 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 1
- 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
- 241001465754 Metazoa Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Herstellung eines Pyranderivates. Es wurde gefunden, dass Verbindungen der allgemeinen Formel
EMI0001.0003
worin R einen gesättigten oder ungesättigten Alkylrest mit mehr als 5 C-Atomen, der am 1. oder 2. C-Atom verzweigt ist, bedeutet, bei geringer Toxizität für den Warmblüter gute bakterizide Wirkungen aufweisen.
Die neuen Verbindungen können gemäss der Erfindung in der Weise hergestellt wer den, dass man Homologe des Acetessigesters ; von der Formel R-CO CH2 COOR', worin R die oben angegebene Bedeutung zu kommt und R' einen niederen Alkylrest dar stellt, bei Gegenwart eines basisch reagieren den Katalysators, vornehmlich Natriumhydro- gencarbonat,
auf 180 bis 220 C erhitzt und den bei der Reaktion sich bildenden Alkohol abdestilliert. Die Umsetzung wird durch fol gendes Formelschema illustriert
EMI0001.0016
Die neuen Verbindungen zeigen eine aus geprägte wachstumshemmende Wirkung ge genüber den verschiedensten Mikroorganismen. Die bakteriostatische Wirkung der einzelnen Glieder ist von der Beschaffenheit des Restes R weitgehend abhängig in dem Sinne, dass die Wachstumshemmung mit steigender An zahl von C-Atomen zunächst zu-, dann ab nimmt.
Bei Verbindungen mit gleicher C- Atomzahl sind aber stets die Glieder mit Ver zweigung am 1. oder 2. C-Atom den entspre- ehenden bekannten Verbindungen mit gerad- kettigem oder andersartig verzweigtem Rest überlegen. Die neuen Pyranabkömmlinge sind somit durch besonders wertvolle Eigenschaften ausgezeichnet und sollen als Desinfektions mittel und zu Heilzwecken Verwendung fin den.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 3-(a-Äthyl- capronyl) - 6 - (a - äthyl-pentyl) -2,3 - dihydro- pyran-2,4-dion, das dadurch gekennzeichnet ist, dass man einen niederen (a-Äthyl-capro- nyl)-essigsäure-alkylester in Gegenwart eines basisch reagierenden Katalysators auf 180 bis 220 C erhitzt und den bei der Reaktion sich bildenden Alkohol abdestilliert.
<I>Beispiel:</I> Der Ausgangsstoff kann folgendermassen hergestellt werden: a-Äth.y,1-capronsäurechlorid (Bulletin de la Societe Chimique de France, Band [4] 33, [1923], Seite 186) wird mit Natriumaeet- essigsäureäthylester kondensiert und der er haltene (a-Äthyl-capronyl) -acetessigsäure- äthylester mit methanolisehem Natriumme- thylat gespalten und umgeentert zu (a-Äthyl- capronyl)
-essigsäure-methclester. Siedepunkt 16 mm/123 bis 125<B>0</B> C.
100 Gewichtsteile (a-äthyl-caprony-1)-essig- säure-methylester und 0,1 Gewichtsteil Na- triumbiearbonat werden 3 Stunden auf 210 bis 215 C erwärmt, wobei etwas Methanol abdestilliert. Durch fraktionierte Destillation wird aus dem Reaktionsgemisch das 3- (a- Äthyl -capronyl) -6- (a-äthyl-pentyl)-2,3-di- hydropyran-2,4-dion vom Siedepunkt 0,03 mm/ 151 bis 153 C isoliert.
Process for the production of a pyran derivative. It was found that compounds of the general formula
EMI0001.0003
where R is a saturated or unsaturated alkyl radical with more than 5 carbon atoms, which is branched on the 1st or 2nd carbon atom, have good bactericidal effects with low toxicity for warm-blooded animals.
According to the invention, the new compounds can be prepared in such a way that homologues of acetoacetic ester; of the formula R-CO CH2 COOR ', where R has the meaning given above and R' represents a lower alkyl radical, in the presence of a basic catalyst reacts, primarily sodium hydrogen carbonate,
heated to 180 to 220 C and distilled off the alcohol formed during the reaction. The implementation is illustrated by the following equation
EMI0001.0016
The new compounds show a pronounced growth-inhibiting effect against a wide variety of microorganisms. The bacteriostatic effect of the individual members is largely dependent on the nature of the residue R in the sense that the growth inhibition initially increases with an increasing number of carbon atoms, then decreases.
In the case of compounds with the same number of carbon atoms, however, the members with branches on the 1st or 2nd carbon atom are always superior to the corresponding known compounds with a straight-chain or otherwise branched radical. The new pyran derivatives are thus characterized by particularly valuable properties and are intended to be used as disinfectants and for medicinal purposes.
The subject of the present patent is a process for the preparation of 3- (a-ethyl-capronyl) - 6 - (a - ethyl-pentyl) -2,3 - dihydro-pyran-2,4-dione, which is characterized in that a lower (a-ethyl-capro- nyl) -acetic acid alkyl ester is heated to 180 to 220 ° C. in the presence of a basic catalyst and the alcohol formed during the reaction is distilled off.
<I> Example: </I> The starting material can be prepared as follows: a-Ethylene, 1-caproic acid chloride (Bulletin de la Societe Chimique de France, Volume [4] 33, [1923], page 186) is mixed with sodium et - ethyl acetate condenses and the (a-ethyl-capronyl) -acetoacetic acid ethyl ester obtained is cleaved with methanolic sodium methylate and reentered to (a-ethyl-capronyl)
-acetic acid methyl ester. Boiling point 16 mm / 123 to 125 <B> 0 </B> C.
100 parts by weight of (a-ethyl-caprony-1) -acetic acid methyl ester and 0.1 part by weight of sodium carbonate are heated to 210 to 215 ° C. for 3 hours, some methanol being distilled off. The 3- (a-ethyl-capronyl) -6- (a-ethyl-pentyl) -2,3-dihydropyran-2,4-dione with a boiling point of 0.03 mm / 151 bis is obtained from the reaction mixture by fractional distillation 153 C isolated.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH296481T | 1951-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296481A true CH296481A (en) | 1954-02-15 |
Family
ID=4489257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296481D CH296481A (en) | 1951-05-29 | 1951-05-29 | Process for the production of a pyran derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296481A (en) |
-
1951
- 1951-05-29 CH CH296481D patent/CH296481A/en unknown
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