What are the other impurities that would be found in the oil of cloves?
I would try to purify the eugenol first before doing anything. The other products in it might be toxic if they are not extracted later.

I think you probably need to vacuum distill it in order to get a decent yield.  I haven't found any evidence saying that you can't though, Douchermann probably knows better then I do so I'd wait till he sees this thread. The reason for vacuum distillation is to probably avoid any rearrangement, or polymerization.

As that is my work up there, I guess I t should throw in here.  I never got good yields using eugneol.  Much better idea is to use something that doesn't have the double bond.


But D is right, don't try to purify it too much.  Every time I did this I end up with a few mls of smokey smelling clear stuff.  I am not 100% sure it was 4AC, as it was never enough to really run in the methylenation rx. 4AC is a real unicorn of a molecule.  Every time you think you have it, it disappears.

Basically, the yields for eugneol are just too low to consider running with all that AlCl3.  You are working off a experiment i did very early on in this line of inquiery.  I shit canned it for good reasons. Their are much better for methoxys without the double bound to work with.  Yields are close to 90% for vanilla and others once you get things right.

TCE incubation is a must if you want good yields.


I have actually back burnered to whole eugenol line of inquiry.  end to end yields are never going to be high enough to justify its wide spread adoption.  The bottle neck is the amount of AlCL3 used....it is just too damm expensive, and I have not had any luck with large scale production of it.

my new hopes are currently with MeOS/methionine, cheaper and much easier to source.

But by all means, please try it out for yourself, you might get it working better than I.


I can say that I am very sure that within a few years alot of people will be making MD's through some sort of demethyl/methylenation process. They will be able to do it at scales and costs the near what people are now getting from S.... And they will be doing it completely under the radar.  All the needs to be found is the right reagent pair.

I know its a bit OT but. Just to report a little fuck off of mine latly about AlCl3

I saturated a toluene/xylene mixture... crap goof off solvent OTC ect...
With Cl. its yellow it stinks ect..

You can put Al in but nothing happens. But activated Al thru HgCl2 on the other hand clears up the chlorine in an instant(10 mins tops)

This means to me that AlCl3 could be made by feeding either Small amount of HgCl2/Al into    
A: dry HCl into an inert solvent(NOT what i used) or \
B:Cl2 into the same inert solvent.

Dry solvents and dryest Atmosphere you can get....

Just thought Id add that since its on the lines of one of my projects at the moment. Trying to do away with the hassles of normal AlCl3 synthesis.

The route would be

eugenol ->isoeugenol -> MHP2P -> HHP2P -> MDP2P

this has all be discussed at PN.

What's the stability of the dihydroxy ketone?  I would hope it's no-where near as rediculous as 4-allylcatechol.

The AlCl3 im attempting to make was done at room temp.

The solvent was saturated with Cl in a rough method and feeding Cl in would be more practical.

Since I just wanted to do a quick test I didnt bother with a Cl generator so I put Ca(OCl)2 into xylene/toluene and driped H2SO4 into it until it took a deep yellow orange color. This was decanted into two seperate test tubes. One received plain old Al foil while the other received HgCl2 activated in MeOH Al. The one with just Al showed almost no change over the next half hour or so. A mild darkening of the Al but not much more. On the other hand the one with the activated Al had completely cleared of the Yellow Cl color and a fine black precipitate was noticed on the bottom of the test tube. Where as there was not enough Cl to sustain it and take all the Al to AlCl3 but I feel a slow and steady feed of Clorine into the mix would steadly produce AlCl3.

Since the first test was done to get a feel and see if it would be worth it I think Iv shown that it will be and tonight I think I will follow up and produce enough to quantify this reaction. My question is if successful what do you guys think would be the best means of purification? Also what would be the best solvent to attempt this in? The mix I used to begin with would be a horrible solvent for this because I think it would be a bad idea to have a lewis acid this powerful around xylene and toluene.

I would say benzene or cyclohexane, but I don't imagine you have easy access to either of those.  Chloroform like vesp suggested might work, or methylene chloride should give decent success

I have tried at length to generate AlCl3 with dry HCL (g) bubbled through a suspension of Al powder.

It does not work as described. I have tried it in a range of solvents.  One big problem I ran into is most Al powder is coated these days.

I have tried at length to generate AlCl3 with dry HCL (g) bubbled through a suspension of Al powder.

It does not work as described. I have tried it in a range of solvents.  One big problem I ran into is most Al powder is coated these days.

The Al powder though wasn't activated, nor was there any AlCl3 present, was there? I think AlCl3 gets the reaction going. What do they coat the Al with? To me it seems like the coating would have dissolved in the solvent.

"I have tried at length to generate AlCl3 with dry HCL (g) bubbled through a suspension of Al powder. "

Have you tried passing dry HCL over the heated  oxide?

Chlorine For the metal,Hcl for the oxide + some heat.

never tried that, but my feeling was it wouldn't really scale well, and I don't need gram quantities, i'm looking for a kg scale prep.