The Vespiary

The Hive => Methods Discourse => Topic started by: amalgum on May 06, 2003, 10:38:00 PM

Title: possible new eugenol demethylation?
Post by: amalgum on May 06, 2003, 10:38:00 PM

A friend of SWIMS uncle (the uncle belonged to the friend, not SWIM) happens to had a Ph.D in organic chemistry, and as a result had a humungous lab tucked away in storage.  Well, due to the uncles passing,  the friend let SWIM pay a couple hundred bucks to go through it and take what I wanted (a KILLER deal btw, glassware and chemicals).
  Well, one of the chemicals found was aminophenol, aka hydroxyaniline.  After using TFSE, SWIM was able to find info on the use of aniline HCl to cleave ethers.  The procedure is rather simple, so I have two questions.
  First, can hydroxyaniline HCl be used for ether cleavage with decent results?
  Which leads me the second question, about usage to cleave the ether on eugenol.  Would it work for eugenol?

Title: Yes, it will probably work.
Post by: Aurelius on May 07, 2003, 10:12:00 AM

Yes, it will probably work. Suggestion: use it in the same manner that Pyridine-HCl in the microwave is used.

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html)

It's the fourth method down. 

Also notice the use of nitrobenzene with catalyst.

Title: yeah
Post by: amalgum on May 08, 2003, 05:10:00 AM

Yeah, I saw that before (SWIM used the AlI3 method from that page).  Thats ironic to cause SWIM was also thinking about it being similar to the pyridine method.  That was gonna be SWIMS method of choice at first, but aluminum and iodine is so much cheaper.

Title: granular Al
Post by: Aurelius on May 08, 2003, 11:29:00 AM

do you have granular Al?  if not, the rxn is harder to carry out (volume of crumpled Al foil)

Title: Yes I already know this.
Post by: amalgum on May 08, 2003, 08:30:00 PM

Yes I already know this.  Don't get me wrong, I'm not dissing the AlI3 method, it is a good method.  I'm just saying that if I can set that aside for awhile, throw some hydroxyaniline HCl and some eugenol in the nuker for shorter reaction times and higher yeild till I run out of hydroxyaniline, then hell yeah!  I think I'm going to have a dream tonight!

Title: Agreed
Post by: Aurelius on May 08, 2003, 09:08:00 PM

I completely agree.  The amine HCl method is much better.  Be sure to write it up for all of us.

Title: Agreed
Post by: amalgum on May 09, 2003, 01:49:00 AM

Dream has been moved to tomorrow, when SWIM can go get some starter fluid.  SWIM'll probably get some new stripper to.  Tried distilling DCM from the shit he has now twice using regular distillation setup via graham condensor.  It seems as if a few drops of DCM come through, and the temp never stops at 40, it just keeps going until it gets to 57, when acetone starts coming.

Title: question
Post by: Daphuk_up on September 03, 2003, 09:06:00 PM

What 'amine HCl' compounds are viable for this procedure?  Methylamine HCl?  Does the larger molecular size (as in triethylamine, a known substitute, and pyridine) directly effect yields?  If so, to what magnitude?

On a slightly off-topic note, what can of yields can be garnered from the AlI3 method sans the quantary ammonium salt catalyst?

Answers much appreciated, sincerely, SWID. :)