CH192015A - Process for the preparation of a lactonic ester with an unsaturated side chain. - Google Patents
Process for the preparation of a lactonic ester with an unsaturated side chain.Info
- Publication number
- CH192015A CH192015A CH192015DA CH192015A CH 192015 A CH192015 A CH 192015A CH 192015D A CH192015D A CH 192015DA CH 192015 A CH192015 A CH 192015A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- lactonic
- side chain
- preparation
- unsaturated side
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- -1 levulinic acid ester Chemical class 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 230000009965 odorless effect Effects 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 2
- 229940040102 levulinic acid Drugs 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WJTCHBVEUFDSIK-NWDGAFQWSA-N (2r,5s)-1-benzyl-2,5-dimethylpiperazine Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC=CC=C1 WJTCHBVEUFDSIK-NWDGAFQWSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Eaktonesters mit einer ungesättigten Seitenkette. Das Hauptpatent betrifft ein Verfahren zur Herstellung des r-Laktons der a-Pentenyl- P-methyl-p-oxyadipinäthylestersäure durch Kondensation eines Lävulinsäureesters mit <I>a,</I> r, 8-Tribrom-n-heptylsäure-äthylester in Gegenwart eines Metalles.
Es zeigte sich, dass man ein Produkt er hält, welches dem Endprodukt des Haupt patentverfahrens ähnlich ist, wenn man an Stelle des dort verwendeten Tribromfettsäure- esters den a, d, e-Tribrom-n-caprylsäure-äthyl- ester verwendet.
Das so erhaltene Produkt ist neu und stellt das r-Lakton der a-Hexenyl-R-methyl- P-oxyadipinäthylestersäure dar. Es bildet ein gelbes, geruchloses Öl vom Kpä =175-190 und dis = 1,045 bis 1,050. Es soll zur Her stellung von 3-Methyl-2(hexen-3-yl)-cyclo- penten-2-on-1 dienen, welches als Riechstoff Verwendung findet.
<I>Beispiel:</I> Zu einem Gemisch von 130 g Lävulin- ester, 270 cm' trockenem Benzol und 133 g mit Jod aktivierten Zinkspänen lässt man unter Rühren beim Kochpunkt des Gemisches 367 g a, a, e-Tribrom-n-caprylsäure-äthylester so zulaufen, dass die Reaktion im Gange bleibt, hält nach beendeter Zugabe noch eine Stunde länger im Sieden und arbeitet auf, indem man abkühlt, Schwefelsäure unter Zu satz von Eis hinzufügt, mit Benzol extrahiert, wäscht, das Benzol abtreibt und den Rück stand im Vakuum fraktioniert.
Man erhält in befriedigender Ausbeute das r-Lakton der a-Hexenyl-,Q-methyl-p-oxy- adipinäthylestersäure. Gelbes geruchloses Öl vom gp6 = 175-190<B>0</B>, d<B>16</B> ,= 1,045-1,050.
An Stelle von Benzol kann auch trockener Äther verwendet werden.
Process for the preparation of an aktone ester with an unsaturated side chain. The main patent relates to a process for the preparation of the r-lactone of a-pentenyl-P-methyl-p-oxyadipinethyl ester by condensation of a levulinic acid ester with 8-tribromo-n-heptylic acid ethyl ester in the presence of a metal.
It turned out that a product is obtained which is similar to the end product of the main patent process if the a, d, e-tribromo-n-caprylic acid ethyl ester is used instead of the tribromofatty acid ester used there.
The product obtained in this way is new and represents the r-lactone of a-hexenyl-R-methyl-P-oxyadipin ethyl ester acid. It forms a yellow, odorless oil with a Kpä = 175-190 and dis = 1.045 to 1.050. It is intended to produce 3-methyl-2 (hexen-3-yl) -cyclo- penten-2-one-1, which is used as a fragrance.
<I> Example: </I> To a mixture of 130 g of levulin ester, 270 cm 'of dry benzene and 133 g of zinc shavings activated with iodine, add 367 ga, a, e-tribromine-n- while stirring at the boiling point of the mixture. ethyl caprylate in such a way that the reaction continues, keeps boiling for an hour longer after the addition and works by cooling, adding sulfuric acid with the addition of ice, extracting with benzene, washing, driving off the benzene and the The residue was fractionated in vacuo.
The r-lactone of a-hexenyl, Q-methyl-p-oxy-adipic ethyl ester acid is obtained in a satisfactory yield. Yellow odorless oil from gp6 = 175-190 <B> 0 </B>, d <B> 16 </B>, = 1.045-1.050.
Instead of benzene, dry ether can also be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE192015X | 1934-12-22 | ||
| CH186538T | 1935-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192015A true CH192015A (en) | 1937-07-15 |
Family
ID=25721364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192015D CH192015A (en) | 1934-12-22 | 1935-03-23 | Process for the preparation of a lactonic ester with an unsaturated side chain. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192015A (en) |
-
1935
- 1935-03-23 CH CH192015D patent/CH192015A/en unknown
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