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All 8 posts Subject: possible new eugenol demethylation? Please login to post Down

amalgum
(Hive Bee)
05-07-03 05:38
No 431868
      possible new eugenol demethylation?

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?

Aurelius
(Hive Addict)
05-07-03 17:12
No 431948
      Yes, it will probably work.

Yes, it will probably work. Suggestion: use it in the same manner that Pyridine-HCl in the microwave is used.
https://www.rhodium.ws/chemistry/methylenation.html
It's the fourth method down.

Also notice the use of nitrobenzene with catalyst.

amalgum
(Hive Bee)
05-08-03 12:10
No 432123
      yeah

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.

Aurelius
(Hive Addict)
05-08-03 18:29
No 432182
      granular Al

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

amalgum
(Hive Bee)
05-09-03 03:30
No 432242
      Yes I already know this.

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!

Aurelius
(Hive Addict)
05-09-03 04:08
No 432249
      Agreed

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

amalgum
(Hive Bee)
05-09-03 08:49
No 432275
      Agreed

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.

Daphuk_up
(Hive Bee)
09-04-03 04:06
No 457109
      question

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. smile

Regal Sir Palladium and the Harlot Chlorine...they make such a cute couple. ^_^

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	All 8 posts		Subject: possible new eugenol demethylation?		Please login to post		Down


		amalgum (Hive Bee) 05-07-03 05:38 No 431868				possible new eugenol demethylation?
						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?



		Aurelius (Hive Addict) 05-07-03 17:12 No 431948				Yes, it will probably work.
						Yes, it will probably work. Suggestion: use it in the same manner that Pyridine-HCl in the microwave is used. https://www.rhodium.ws/chemistry/methylenation.html It's the fourth method down. Also notice the use of nitrobenzene with catalyst.



		amalgum (Hive Bee) 05-08-03 12:10 No 432123				yeah
						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.



		Aurelius (Hive Addict) 05-08-03 18:29 No 432182				granular Al
						do you have granular Al? if not, the rxn is harder to carry out (volume of crumpled Al foil)



		amalgum (Hive Bee) 05-09-03 03:30 No 432242				Yes I already know this.
						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!



		Aurelius (Hive Addict) 05-09-03 04:08 No 432249				Agreed
						I completely agree. The amine HCl method is much better. Be sure to write it up for all of us.



		amalgum (Hive Bee) 05-09-03 08:49 No 432275				Agreed
						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.



		Daphuk_up (Hive Bee) 09-04-03 04:06 No 457109				question
						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. Regal Sir Palladium and the Harlot Chlorine...they make such a cute couple. ^_^

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