CH91087A - Process for the preparation of heliotropin from isosafrole. - Google Patents
Process for the preparation of heliotropin from isosafrole.Info
- Publication number
- CH91087A CH91087A CH91087DA CH91087A CH 91087 A CH91087 A CH 91087A CH 91087D A CH91087D A CH 91087DA CH 91087 A CH91087 A CH 91087A
- Authority
- CH
- Switzerland
- Prior art keywords
- isosafrole
- heliotropin
- weight
- parts
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Heliotropin aus Isosafrol. Im Hauptpatent ist ein Verfahren zur Darstellung von Vanillin aus Acetylisoeugerrol durch Oxydation beschrieben, welches darauf beruht, dass man die Oxydation in Gegenwart von aromatischen Aminocarbonsäuren, wie z.B. Para-arninobenzoesäure, ausführt und das Vanillin durch Verseifung herstellt.
Es wurde nun gefunden, dass der Oxyda- tionsprozess beim Isosafrol, das ebenfalls eine oxydierbare Propenylgruppe enthält und als Endprodukt Heliotropin ergibt, ähnlich ver läuft wie beim Acetylisoeirgerrol.
Vorliegende Erfindung betrifft demnach ein Verfahren zur Darstellung von Heliotropin aus Isosafrol, welches darauf beruht, dass man die Oxydation in Gegenwart von aromatischen Aminocarbonsäuren durchführt. Man kann auch solche Verbindungen der Aminocarbon- säuren zusetzen, wie z. B. Salze und Ester, welche bei den Reactionsbedingungen in die Aminocarbonsäure übergehen.
<I>Beispiel:</I> 240 Gewichtsteile Natriumbichromat wer den in 1000 Gewichtsteilen Wasser gelöst und darin 120 Gewichtsteile Isosafrol mittelst Rührwerk fein verteilt. Dazu lässt man eine Lösung von 10 Gewichtsteilen Para-amino- benzoesäure, gelöst in 480 Gewichtsteilen 500,'0 Schwefelsäure, zufliessen unter Innehaltung einer mittleren Temperatur.
Nach beendeter Oxydation extrahiert man das gebildete Helio- tropin mit einem Lösungsmittel und entzieht es mit Hilfe von Bisulfitlösung dieser Lösung. Die gereinigte Bisulfitverbindung wird mit Säuren oder Alkalien zersetzt und das Helio- tropin in sehr reiner Form gewonnen.
Auf diese Weise erhält man 14 Gewichtsteile unverändertes Isosafrol und 90 Gewichtsteile Heliotropin, während man ohne den Zusatz von Para-aminoberrzoesäur-e 44 Gewichtsteile unverändertes Isosafrol und 50 Gewichtsteile Heliotropin erhält.
Die Konzentrationsbedingungen und die Art der Ausführung des Verfahrens können varieren. Man kann zum Beispiel auch mit Chromsäure in Gegenwart von Wasser oder Essigsäure arbeiten; stets zeigt es sich, dass eine glattere Oxydation beim Zusatz von Para-amirroberrzoesäure stattfindet.
Process for the preparation of heliotropin from isosafrole. The main patent describes a process for the preparation of vanillin from acetylisoeugerrol by oxidation, which is based on the fact that the oxidation is carried out in the presence of aromatic aminocarboxylic acids, such as e.g. Para-arninobenzoic acid, and the vanillin is produced by saponification.
It has now been found that the oxidation process in isosafrole, which also contains an oxidizable propenyl group and gives heliotropin as the end product, proceeds in a similar way to acetylisoeirgerrol.
The present invention accordingly relates to a method for the preparation of heliotropin from isosafrole, which is based on the fact that the oxidation is carried out in the presence of aromatic aminocarboxylic acids. You can also add compounds of the aminocarboxylic acids, such as. B. Salts and esters which convert into the aminocarboxylic acid under the reaction conditions.
<I> Example: </I> 240 parts by weight of sodium dichromate are dissolved in 1000 parts by weight of water and 120 parts by weight of isosafrole are finely distributed in it by means of a stirrer. For this purpose, a solution of 10 parts by weight of para-aminobenzoic acid, dissolved in 480 parts by weight of 500.0 sulfuric acid, is allowed to flow in while maintaining a medium temperature.
When the oxidation is complete, the heliotropine formed is extracted with a solvent and removed from this solution with the aid of bisulfite solution. The purified bisulfite compound is decomposed with acids or alkalis and the heliotropine is obtained in a very pure form.
In this way, 14 parts by weight of unchanged isosafrole and 90 parts by weight of heliotropin are obtained, while 44 parts by weight of unchanged isosafrole and 50 parts by weight of heliotropin are obtained without the addition of para-aminoberzoic acid.
The concentration conditions and the manner in which the process is carried out can vary. For example, you can also work with chromic acid in the presence of water or acetic acid; it is always found that a smoother oxidation takes place with the addition of para-amirroberzoic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH89053T | 1919-09-09 | ||
| CH91087T | 1919-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH91087A true CH91087A (en) | 1921-10-17 |
Family
ID=25703926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH91087D CH91087A (en) | 1919-09-09 | 1919-09-09 | Process for the preparation of heliotropin from isosafrole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH91087A (en) |
-
1919
- 1919-09-09 CH CH91087D patent/CH91087A/en unknown
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