Methylene p m dioxybenzylglycol [ safrole glycol ]
forms up to 50% from the applied Safrole, if one warms up safrole with an 1,5 percent
Chamäleonsolution 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.
Methylene-p-m-dioxybenzylglycol Diacetate [safrole glycol diacetate]
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.
a-Homo piperonylacid, [3,4-methylenedioxyphenylacetic acid]
Here follows a strange part:
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:
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.
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
Ligroien (for what the fuck that may be.)
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.
REMEMBER I AM NOT A BERLINER (READ GERMAN!!!!) They are only my neighbours.