After adding the combination of eugenol/PTC/bitofsolvent dropwise to the stirring but cold AlI3 suspension the mixture was refluxed for about 30minutes, then cooled to about 5C with lots of stirring to stop the suspension settling, then the entire mix was poured into 2M HCl (i was doing a 19.2g eugenol trial and dumped the whole thing into 200ml acid), vigorous stirring was applied for a five minutes then the mixture left for the layers to seperate, three layers formed, a bubbling water/grey suspension layer on the bottom, the bubbles were dragging some of the suspension to the top were they would promtly fall back down. The top layer was the cyclohexane (oh i changed solvents for this trial) and inbetween the two layers was a black crystalline mass with specks of red in it. The bubbling continued for some thirty minutes (it was not solvent boiling off as the mix was only warm to touch and anyway it was generated in the lower water layer not the solvent layer), i don't think it was Me-I (bp?) so what was the mystery gas???
Anyway after the gas had stopped i filtered off the mass in the interface, separated the layers and removed the solvent, the cyclohexane had a small mass(~2g) of black gooey tar dissolved in it, the water when evporated on a water bath (my rot evap is fucked) produced a white crystalline mass on top of the water as the water evaporated (ie allylpyrocatechol is sparingly sol?, the water/air interface is cold enough for it to crystallise, i am clutching at straws?), I then went home because it was late and i was tired and had an exhibition to go to, then i went to this bar and meet this girl that i had spoken to a few times, she was nice, we chatted, she bought me a drink, we went to another bar, we played with each others hands, we kissed, we went back to her house, oh yes the workup, when I got back in in the morning the white crystalline mass had turned black and tarry and the whole thing looked shot. Whilst doing a vacuum distil I got hungup on the IR and forgot about it, it was rather a sorry mess when i got back there, but i could see the presence of some of those purpley crystals which i think are the Al-goodbit complex. Anyway will start again tommorrow after that fuckup.
Also though, i ran a trial using iodine and aluminium foil (cut in thin slivers) instead of the 5micron aluminum powder i was using. the foil worked fine.
Has anyone tried using HI to cleave this bastard, you could form it insitu from the insitu created AlI3 by keeping the mix cool (ie don't go to reflux) and dropping water in.
Anyway will try again another day, i need to do some legit work next week, don't have any safrole at present so I have to wait for the RuCl3 and catalyic converter trial on the benzo wacker, good luck mr/mrs/miss/ms/dr/prof/rev/mc/mp kitty-man, crack it next week so i can move on to the methylene bridge reaction, i am bored of the cleavage shit.
Sorry just re-read your post there are some problems with the ease in which you describe the workup, firstly the organic layer also has residual iodine in it, secondly the allypyrocatechol has some solubility in water.
Basically what happens when you make the AlI3 is that you mix the iodine/al/solvent at room temp the whole thing goes bright purple, you then reflux and stir for a couple of hours, the solution goes clear with a finely dispersed grey suspension wizzing around, next you need to cool it in order to add the eugenol, cooling seems to decompose some of Ali3 and the solution turns reddy again, then when you begin to add the eugenol the whole things turns dirty orange but for some reasom the iodine after hydrolysis wants to stay in the organic layer (is this normal?), giving it a red colour.
A further point, sorry this is a very long post, someone gave me a demethylation method where the aryl ether is dropped into a ALCl3/NaCl (5:) melt at about 150C, left for about three minutes then dumped into icewater, its all done under N2, anyone had any experience with this reaction, it sure sounds quick and easy. Yeah you say a quick and easy way to make tar.
OK I am going now
blue always
except for at the start