Purification of 4-methoxyphenol

biobrew · Sat May 07, 2005 8:20 pm

Am i really going to distill this? 4-methoxybenzaldehyde was converted to the o-formyl-4-methoxybenzaldehyde via performic in DCM. The the formyl group was lysed via NaOH and now i am left with brown goo/crystals. Can i wash the byproducts with something? I was hoping to wash then crystalize(ethylacetate?), but if any other bees have distilled this, let me now. I followed the 4-methoxyphenol synth from rhodiums site.

brain · Linguist Extraordinaire

I have wery much p-methoxyphenol[~6 kg] , wery pure, but if you want i can try to recrystalize it or destill ... but pure product will behawe different i thik-and i dont know if these will be helpfull for you...

biobrew · Sun May 08, 2005 2:27 am

I am leaning towards running some slubility tests then trying to crystalize, and maybe distill after that. But i really don't want to start heating it w/all the byproducts.

atarax · Mon May 09, 2005 8:12 am

I saw some reference to "not posting references" somewhere back before registering, but I'll just say that the latest literature reference I've seen talked about purifying p-methoxyphenol by prep TLC. I suppose that translates to column chromatography for larger scales. Tough break.

fogged · Mon May 09, 2005 6:39 pm

I would suggest purifying it by sublimation... a xylene extraction of p-MeO-phenol, with most solvent removed under vacuum, and then allowed to stir on low heat overnight to remove the remainder, resulted in a lovely crop of beautiful white needles of the phenol around the rim of the beaker (and I cringe to think how much was lost in this manner!). Perhaps if you tried doing this, but with a cold finger condenser (or something improvised to be like one), as you would if resubliming iodine or similar?

Cant be certain that this will work, but it has to be easier than a column and is therefore worth a go!

biobrew · Tue May 10, 2005 4:35 am

Well tomorrow is the day, so we'll see what happens Rolling Eyes

Is this a listed compund? This has been a fun project, but can I avoid it? I am going to start off with solubility test, then the sublimation idea sounds interesting. And unfortunatly, the only column that i have right now is a sephadex column on a beautiful HPLC machine. Oh how it tortures me when i look at it Crying or Very sad

biobrew · Fri May 13, 2005 7:06 am

I swear i am going to stop replying to my own posts Very Happy

So, after running 10 sollublity tests, Mr PhD came-a-long with his magic book and voila. Are you ready.....drumroll.......dihydrogen monoxide....yep, water. It took a bit more than i wanted, but it came through. It really wanted to oil-out, and on top of that, so did the black-red byproduct. Once i thought that all my goods went into into solution, i pipetted the goo out and cyrstallized, blammo. A slight rosed colored waxy white solid that was flaky. Sorry to take up everybodies time, but hope this is some contribution.