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Rhodium
(Chief Bee)
12-09-01 20:09
No 246004
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safrole glycol & 3,4-MD-phenylacetic acid (German)
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Methylen-p-m-dioxybenzylglykol [safrole glycol]<br><br>bildet sich bis zu 50% des angewandten Safrols, wenn man Safrol mit einer auf 70-80°C erwärmten 1.5 procentigen Chamäleonlösung unter Anwendung von 5 Theilen Kaliumpermanganat auf 2 Theile Safrol bis zur Entfürbung schüttelt. Man filtrirt vom ausgeschiedenen Mangansuperoxydhydrat, extrahirt das Filtrat mit Aether, schüttelt die Aetherauszüge mit saurem, schwefligsaurem Natrium, um kleine Mengen gleichzeitig gebildeten Piperonals daraus zu entfernen, verdampft den Aether and krystallisirt den Rückstand aus siedendem Benzol. Man erhhält das Methylen-p-m-dioxybenzylglykol auf diese Weise in weissen, bei 82-83° schmelzenden Nadeln, welche sich leicht in siedendem Wasser and Aether, schwerer in Alkohol and Benzol lösen, von Chloroform and Aceton ebenfalls aufgenommen and aus der Benzollösung durch Ligroïn gefüllt werden.<br><br>Diacetat des Methylen-p-m-dioxybenzylglykols [safrole glycol diacetate]<br><br>Diese Verbindung bildet sich, wenn man das obige Glykol unter Zusatz von etwas Natriumacetat mit ûberschüssigem Essigsü,ureanhydrid etwa 2 Stunden am Rückflusskühler erhitzt. Das Reactionsproduct wird wiederholt mit Wasser and verdünnter Sodalüsung gewaschen. Man erhâlt auf diese Weise das Diacetat des Methylen-p-m-dioxybenzylglykols in Gestalt eines hellgelben Oeles von schwach aromatischem Geruch, welches. bei 15-20 mm Druck um 240°C unzersetzt übersiedet.<br><br>a-Homo piperonylsàure, [3,4-methylenedioxyphenylacetic acid]<br><br>Wenn bei Einwirkung oxydirender Agentien auf Safrol zuerst die Elemente des Wassers im Sinne der Formel [...] addirt werden, oder wenn -alsbald das hierüber beschriebene Glykol entsteht, so muss sich bei weiterer Oxydation der einen oder anderen Verbindung zunâchst a-Homopiperonylsâure bilden. Das ist in der That der Fall. Die a-Homopiperonylsâure kann durch directe Oxydation des Safrols leicht erhalten werden, wenn man dabei âhnliche Bedingungen innehâlt, wie Nagai and ichi) sie vor lângerer Zeit für die Darstellung von a-Homovanillinsü,ure aus Aceteugenol angegegeben liaben. Man verfü,hrt zweckmâssig wie folgt:<br><br>Man schüttelt 5 Theile Safrol mit der auf 70-80°C erwârmten AuH5sung von 12.5 Theilen Kaliumpermanganat and 5 Theilen Eisessig in 1000 Theilen Wasser. Nach eingetretener Entfârbung macht man mit Natronlauge alkalisch, filtrirt vom ausgeschiedenen Mangansupèroxyhydrat ab and schüttelt mit Aether aus , um das gebildete Piperonal zu entfernen. Die alkalische LSsung wird darauf bis auf ein Viertel ihres ursprünglichen Volumens eingedampft, mit Schwefelsü,ure angesüuert and mit Aether ausgezogen. Der Rückstand vom Aetherauszuge, welcher a-Homopiperonylsü,ure and Piperonylsü,ure enthâlt, wird mit Wasser and Magnesiumcarbonat gekocht and die dadurch erhaltene LSsung der Magnesiumsalze der obigen Sâuren behufs Entfernung harziger Verunreinigungen mit Aether geschüttelt. Der so gereinigten Salzl5sung entzieht man nach dem Ansü,uern mit Schwerelsâure die darin vorhandenen beiden organischen Süuren wiederum durch Aether and krystallisirt den Aetherrückstand aus 5 Theilen siedenden Wassers um, wobei wesentlich nur a- Homopiperonylsüure in LSsung geht.<br><br>Die durch methodisches Umkrystallisiren aus siedendem Wasser gereinigte a-Homopiperonylsüure bildet weisse Nadeln and schmilzt bei 127-128°C. Sie löst sich leicht in siedendem Wasser, Alkohol, Aether, heissem Benzol, Aceton and ist in Ligroïn nabezu unlöslich.<br><br>Reference: Berichte 24, 2879 (1891)
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boppesz<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-10-01 02:13</span><br>
<span title="Link to this post by using the markup [246076]">No 246076</span><br>
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<title>Re: safrole glycol & 3,4-MD-phenylacetic acid (German)
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Was ist denn Chamäleonlösung am English?
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">12-10-01 04:51</span><br>
<span title="Link to this post by using the markup [246087]">No 246087</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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I have no idea. I was hoping someone would translate the article for us.
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boppesz<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-10-01 04:55</span><br>
<span title="Link to this post by using the markup [246088]">No 246088</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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Hmm thought you were German. I will translate it, but it will take me till tonight before I have finished this.
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">12-10-01 05:24</span><br>
<span title="Link to this post by using the markup [246090]">No 246090</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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I can read some german, but it takes just too long for me to translate more than two paragraphs (I'm not good at doing "rough" translations, I'm too perfectionist for that).
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boppesz<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-10-01 11:45</span><br>
<span title="Link to this post by using the markup [246155]">No 246155</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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Methylene p m dioxybenzylglycol [ safrole glycol ] <br><br>forms up to 50% from the applied Safrole, if one warms up safrole with an 1,5 percent <font color="red">Chamäleonsolution</font color="red"> to 70-80°C with the use of 5 parts potassium permanganate and 2 parts Safrole up. Stir till precipitate forms (90 % sure of this translation). Filter off separated manganese"super"oxidehydrate (dunno what the super means), extract the filtrate with ether, treat the ether single dumps with acid and sodiumsulfate in order to remove small quantities of piperonal which is formed also, evaporate the ether and crystallize from boiling benzene. Safroleglycol is formed this way: white needles melting at 82-83°, which easily dissolves in boiling water and ether, more difficult in alcohol and benzene, dissolves in chloroform and acetone.<br><br>Methylene-p-m-dioxybenzylglycol Diacetate [safrole glycol diacetate]<br><br>This compound forms, if one refluxes above glycol under addition of some sodiumacetate with acetic anhydride for 2 hours. The Reactionproduct is washed several times with water and with diluted Sodasolution (NaOH will work I think). In this way the diacetate of safrole is formed: an oil with a weakly aromatic smell, lightyellow, which comes over at 240 °C at 15-20 mm without decomposition.<br><br>a-Homo piperonylacid, [3,4-methylenedioxyphenylacetic acid]<br><br>Here follows a strange part:<br><br>If safrole is treated with oxidizing agents after addition of water in the sense of the formula [... ], or if - immediately glycol as described above develops, then a-Homopiperonylacid must be formed with further oxidation or for certain compounds. That is the case here. The a-Homopiperonylacid can be formed easily by direct oxidation of the Safrole, if one performs thereby different conditions, (like Nagai and Ichi) DON'T UNDERSTAND THIS PART, BUT I THINK IT'S NOT IMPORTANT, work as follows:<br><br>One stirrs 5 parts Safrole with a warmed solution (70-80°C) of 12.5 parts potassiumpermanganate and 5 parts glacial acetic acid, in 1000 parts water. After discolouration occurs make alkali with NaOH, filter off separated mangansupèroxyhydrate wash with ether in order to remove the formed Piperonal. The alkaline solution is evaporated up to a quarter of its original volume, treated with sulfuric acid, and extracted with ether. The ether single dumps which contain a-Homopiperonylacid and Piperonylacid, are boiled with water and magnesiumcarbonate and the solution of the magnesiumsalts of the above acids is washed with ether to remove resinlike impurities. The in such a way cleaned solution of salts is made acidic again with sulfuric acid and washed again with ether. The ethersolution is recrystalized with 5 parts boiling water. Now only the a-homopiperonylacid goes in solution.<br><br>The a-Homopiperonylsueure cleaned by recrystalization from boiling water forms white needles and melts at 127-128°C. It solves easily in boiling water, alcohol, ether, hot benzene, acetone and is insoluble in <font color="red">Ligroien</font color="red"> (for what the fuck that may be.) <br><br>The translation is okay except from the very strange middle part. I don't think this is really important for the procedure, only for a little understanding. I can't translate the red words, and I am not quite sure that Entfürbung means precipitation, but I think it is.<br><br><font color="red">REMEMBER I AM NOT A BERLINER (READ GERMAN!!!!) They are only my neighbours. <img src="../forum/images/icons_lightgrey/crazy.gif" alt="crazy" title="Crazy" heigth="15" width="15"></font color="red">
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psyloxy<br>
<i>(<span title="The user's title at the time of posting">Hive Addict</span>)</i><br>
<span title="Posting date">12-10-01 11:57</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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Chamäleonlösung is just that 1.5% KMnO4 solution. It changes its color<br>from red/orange to blue all the time ... hence the name chamäleon-solution.<br>I don't know the word for chamäleon but you all surely know those<br>reptiles that can change their color with their environment... they also<br>move very slowly...<br><br><br>--<b>psyloxy</b>--
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">12-10-01 12:13</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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Ligroien = Ligroin = Petroleum ether. The intermediate <font color="red">[...]</font color="red"> is MDP2Pol.
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<font color="#ff0000">lugh</font><br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-10-01 12:15</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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Even <a href="http://www.chemie.de/tools/dictionary/" target="_blank" title="Jump to this external site">http://www.chemie.de/tools/dictionary/</a> doesn't seem to be much help this time, but Ligroien seems like the German equivalent for the English Ligroin, another name for petroleum ether aka hexanes, heptanes etc.
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hypo<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-10-01 13:07</span><br>
<span title="Link to this post by using the markup [246190]">No 246190</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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it's called ligroin in german to. but this text is very old and has a very strange syntax.<br><br>entfärbung=discoloration.
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boppesz<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-11-01 08:11</span><br>
<span title="Link to this post by using the markup [246465]">No 246465</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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yes, entfarbung. But what about entfurbung? that's what the patent says
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hypo<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-11-01 08:19</span><br>
<span title="Link to this post by using the markup [246467]">No 246467</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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print error or more probably scan error.
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boppesz<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-11-01 08:58</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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The intermediate [...] is MDP2Pol. <br><br>Which intermediate are you talking about?
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">12-11-01 10:10</span><br>
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<b title="The subject of this post">Re: safrole glycol & 3,4-MD-phenylacetic acid (German)</b>
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The oxidation intermediate that was depicted in the original reference, and substituted with [...] in the german text above.
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