Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: 3,4 dihydroxyphenyl ethanol (Hydroxytyrosol)
idontlie
Harmless
*




Posts: 15
Registered: 3-1-2010
Member Is Offline

Mood: No Mood

[*] posted on 14-5-2010 at 17:20
3,4 dihydroxyphenyl ethanol (Hydroxytyrosol)


3,4 dihydroxyphenyl ethanol is kinda cool, a powerful antioxident and otc and all that but i'd like to synth it. Why? Cause I'm a 'tarded nerd.

I first was thinking about ethyl glycol to 1-chloro 2-hydroxyl ethane via lucas' reagant (probably wont work), pcl3 or w/e ended up working (i know shit yields for the mono). then grignard to chloro - catechol (lol yeah i was like fuck maybe this was a terrible idea and should just get olive oil and be happy, pretending i accomplished something)

Then I decided maybe its time to buy some eugenol and try this who methylating demethylating thing (with aluminum iodine). "My idea" is like this eugenol -> protection maybe with methyl halide, if needed to prevent permaginate from forming quinone. Does this even happen, I feel it might and I'm not really sure it would effect anything except change the amount of permaginate I think I would need-> Potasium Permaginate oxidative cleavage, leaving me with hopefully an alcohol (huhu yeah right, cleavage is to aldehydes I know) but more likely an aldehyde and carboxylic acid, seperate aldehyde (If im lucky i will be able to a/b if not concentrate and percipitate out the lithium salt of the acid or the adjunct of the aldehyde) -> Al/Hg -> Aluminum Iodide Deprotection -> Feel like a happy nerd.

What to do with product? Fuck if I know, Im not gonna eat anything I make. Probably just try and ignite it.

What do you think of this as a summer fun project?

-----------
edit1:

Same train of thought what does the chloroform test leave on a ketone? Ie bleaching the 3,4-dimethoxy phenyl-2-propanone an aldehyde, acyl chloride or something else?

edit2:

Im gonna stop posting for a while why i sit n ponder but the answer was something else (carboxylic acid)

[Edited on 15-5-2010 by idontlie]

[Edited on 15-5-2010 by idontlie]
View user's profile View All Posts By User
bbartlog
International Hazard
*****




Posts: 1139
Registered: 27-8-2009
Location: Unmoored in time
Member Is Offline

Mood: No Mood

[*] posted on 14-5-2010 at 20:29


Quote:
What do you think of this as a summer fun project?


I think your vague schemes to manufacture phenethyl-presumably-amines are very unlikely to succeed. And while I hold no animus against people who want to make stuff that may or may not be legal where they live, I get irritated when people adopt a pretense so transparent that it's an insult to our intelligence. You made three or four attempts to extract piperidine and now mention 3,4-dimethoxy-phenyl-2-propanone, but you want us to believe that this is all just about a fun summer chemistry project. If we were that retarded, we wouldn't be able to help you anyway.
Anyway, your question is too much of a stream of consciousness dump of what looks like a whole bunch of questions. The short answer is no, to the extent there is a plan in there, it won't work. More detailed answers would require better detailed questions.
View user's profile View All Posts By User
idontlie
Harmless
*




Posts: 15
Registered: 3-1-2010
Member Is Offline

Mood: No Mood

[*] posted on 15-5-2010 at 02:11


Quote: Originally posted by bbartlog  


I think your vague schemes to manufacture phenethyl-presumably-amines are very unlikely to succeed. And while I hold no animus against people who want to make stuff that may or may not be legal where they live, I get irritated when people adopt a pretense so transparent that it's an insult to our intelligence. You made three or four attempts to extract piperidine and now mention 3,4-dimethoxy-phenyl-2-propanone, but you want us to believe that this is all just about a fun summer chemistry project. If we were that retarded, we wouldn't be able to help you anyway.
Anyway, your question is too much of a stream of consciousness dump of what looks like a whole bunch of questions. The short answer is no, to the extent there is a plan in there, it won't work. More detailed answers would require better detailed questions.


So I am locked to only one small sector of chemistry? I honestly was under the assumption that anyone is capable of anything and that we should have the respect that maybe, just maybe people all are not liars. If I wanted the amines I would have asked about them, 3,4-dimethyl phenyl ethyl amine isnt a listed substance, sounds like fair game to ask about if I had wanted it.

Why is a phenyl-2-propanone only usable for amine production? It was an after though when I thought of the haloform test. I thought it could be used to strip a methyl off and leave me with something readily reducible to the alcohol I want.

If i wanted to make an amine from eugenol Id ethylate via diethyl sulfate, oxidise to the 3-methoxy 4-ethoxy -phenyl-2-propanone stir with hydroxylamine-hcl, collect oxime reduce via Al/K2HgI2 (I2/KI-sulfuric acid solution and mercury stir for three days.) and gas. Its a mild anti-depressant when used with a maoi-a with no recreational attraction. If I wanted the phenyl ethyl amine Id start with vanillin go see mister henry with nitromethane then attempt a zn/hcl reduction. All these are rather well documented and boring. Even the magical "md" derivitive, 3,4-methylenedioxy phenyl ethyl amine, also happens to be not of interest for the same limited mental activeness. But I don't unless these amines will get me to the alcohol, which I don't count on happening.

But hey thanks bro, when Ive got my thoughts better together Ill ask more true question. Sorry for wasting your two cents on a reply.

[Edited on 15-5-2010 by idontlie]
View user's profile View All Posts By User
Nicodem
Super Moderator
Thread Moved
15-5-2010 at 13:18
smuv
International Hazard
*****




Posts: 842
Registered: 2-5-2007
Member Is Offline

Mood: Jingoistic

[*] posted on 16-5-2010 at 15:56


Its not the easiest compound to make sticking with OTC reagents. The biggest issue I see is accidentally oxidizing the quinol to the quinone.

Maybe if I were to do it:

1: catechol to 3,4-dihydroxyacetophenone: catechol, AcOH ZnCl2
2: acetophenone to the phenacylhalide: any method you want

From here we could take two routes

3a. phenacyl halide to the a-hydroxyacetophenone: ?? sodium carbonate or acetate in DMSO
4a. a-hydroxyacetophenone to the 2-phenylethanol: reduction in ethanol containing a few eq of HCl with Pd/C under 1 atm hydrogen

or

3b. phenacyl halide to the 2-phenylhaloethene: same as above
4b. hydrolysis to the alcohol: same as 3a??

The reduction of the phenacyl chloride will be easier than the a-hydroxyacetophenone. The hydrolysis of the phenacylhalide will be easier then the 2-phenylhaloethane.




"Titanium tetrachloride…You sly temptress." --Walter Bishop
View user's profile View All Posts By User
entropy51
Gone, but not forgotten
*****




Posts: 1612
Registered: 30-5-2009
Member Is Offline

Mood: Fissile

[*] posted on 16-5-2010 at 17:12


Quote: Originally posted by idontlie  
If i wanted to make an amine from eugenol Id ethylate via diethyl sulfate, oxidise to the 3-methoxy 4-ethoxy -phenyl-2-propanone stir with hydroxylamine-hcl, collect oxime reduce via Al/K2HgI2 (I2/KI-sulfuric acid solution and mercury stir for three days.) and gas.
As if you have eugenol, vanillin, diethyl sulfate, hydroxylamine or any of the other chemicals your little brain fantasizes about. Not hard to recognize a mentally masturbating chemical weenie. We see them here every frickin day.
View user's profile View All Posts By User
zed
International Hazard
*****




Posts: 2273
Registered: 6-9-2008
Location: Great State of Jefferson, City of Portland
Member Is Offline

Mood: Semi-repentant Sith Lord

[*] posted on 19-5-2010 at 01:35


On the other-hand, you could attempt to react tyrosine with iodine.

Attempting to form a mono-halogenated product. Nope, I don't know what reaction conditions would be required, but 3,5-di-iodotyrosine is done easily.

Then convert, the 3-iodo-tyrosine to 3-hydroxy-tyrosine. Reaction with NaOH should do it.

Thereafter, the resultant 3,4-dihydroxy-phenylalanine....Might be converted to the Phenethylamine via decarboxylation. Refluxing in acetophenone or in the presence of another high boiling ketone.....facilitates such decarboxylations.

Conceivably, the phenethylamine could then be reacted to produce the phenethyl alcohol. Diazotization would be ideal, but unfortunately, straightforward diazotization usually isn't very successful at directly converting aliphatic amines into alcohols.


If only you wanted the amino-acid or the amine. It would be so much simpler.



[Edited on 19-5-2010 by zed]
View user's profile View All Posts By User
Paddywhacker
National Hazard
****




Posts: 478
Registered: 28-2-2009
Member Is Offline

Mood: No Mood

[*] posted on 19-5-2010 at 21:57


Quote: Originally posted by entropy51  
As if you have eugenol, vanillin, diethyl sulfate, hydroxylamine or any of the other chemicals your little brain fantasizes about. Not hard to recognize a mentally masturbating chemical weenie. We see them here every frickin day.


ROTFLOL .... Snort!

Entropy, you have one wickedly sharp tongue in your head.
View user's profile View All Posts By User
497
International Hazard
*****




Posts: 778
Registered: 6-10-2007
Member Is Offline

Mood: HSbF6

[*] posted on 25-5-2011 at 00:51


How about just react L-DOPA with bleach and then reduce the aldehyde to the alcohol with something like sodium dithionite or many others? The yield of the aldehyde may be improved by using an alkyl hypochlorite instead of bleach and/or O protecting the catechol oxygens, many options for this too. I wonder if things like TCCA couldn't be used also? If you don't want to buy L-DOPA (it is a bit pricey) then you can get it in moderate yields from the very cheap L-tyrosine by oxidation with H2O2+FeSO4. Pretty convenient if you ask me.
View user's profile View All Posts By User
peach
Bon Vivant
*****




Posts: 1428
Registered: 14-11-2008
Member Is Offline

Mood: No Mood

[*] posted on 28-5-2011 at 02:03


You can decarboxylate tryptophan relatively easily by refluxing it in DMSO with various acetate salts, apparently. You can change the solvent as well, but the reference I'd seen was specifically using DMSO because it was easier than the alternatives. I tried it with 5-HTP wondering if I might be able to get towards an ampoule of serotonin so I can make a 'brain in a box' collection. But I seem to remember it wasn't evolving gas as quickly as it should have been. I never got round to finishing that; flask was a nice indigo blue colour about a month later. I will likely give it another go but am having fun with my tube furnace and various other things at the moment.

If it works with tryptophan, it may function to swap L-DOPA to dopamine, and you can go from there.

Here's a picture of the results from dripping eugenol onto AlI3;

The three different plates are me shifting the balance of solvents they're eluted with (towards none polar I think). Other than that, they're all the same.

Spot A is eugenol
B is the result of this experiment
C is the result from another version of it I think

The stain is ferric chloride, for the phenol groups.

Things to note

The eugenol spot is light purple and the results are a much darker suggesting more phenol groups may have opened.

The spot B is lagging quite a long way behind the Eugenol spot A on the third plate, so they're not the same thing.

There are only faint traces of a spot on B and C that are near to that of A, suggesting the majority of the eugenol has reacted.

There are some other bands in there, but not a continual smear that would suggest continuous chain polymerisation. However, I was never able to get the result to solidify at room temperature as chemspider suggests it should, only when cooled. And it would usually be a light brown rather than the tan / beige colour it'd be during the experiment. Over time, left open to the atmosphere, it would become almost black, indicating it is atmospherically sensitive and that the entire workup, filtration included, probably wants doing as air free / inert to get that room temperature tan solid.

Please don't PM me asking how to make RexTasy Sweets; most first year chemistry students are self-proclaimed geniuses, so get on with going to jail with some actual practicals of your own rather than speculation from labs someone else has written for you





View user's profile View All Posts By User

  Go To Top