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Keftedes89
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[*] posted on 3-12-2014 at 02:34
Will this Reaction Work?


I am trying to make good leaving groups out of the alcohol groups in dihydroxyacetone. The problem is, I don't like working with overly hazardous materials that will kill me. I avoided the common agents that convert primary alcohols to primary haloalkanes because I don't want to deal with dichloroacetone, dibromoacetone, or diiodoacetone.

I want to know if I can use tosyl-chloride to substitute the alcohol groups for tosyl groups. Will this reaction work or will the ketone functional group make for some trouble? Finally, is there another method I can use to convert the -OH to a safe leaving groups that wont create a compound that will kill me?

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[*] posted on 3-12-2014 at 05:18


I don't see why not. Solubility may be an issue. And pyridine isn't exactly harmless (if you're a male).
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Nicodem
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3-12-2014 at 08:15
zed
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[*] posted on 7-12-2014 at 15:52


Dunno. Got not idea what you are up to.

Now, Acetone Dicarboxylic Acid, isn't terribly difficult to decarboxylate. Does this help?

Easy enough to make. Though some opinions differ.

http://www.orgsyn.org/demo.aspx?prep=cv1p0010

[Edited on 7-12-2014 by zed]
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Chemosynthesis
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[*] posted on 7-12-2014 at 16:19


Quote: Originally posted by zed  

Now, Acetone Dicarboxylic Acid, isn't terribly difficult to decarboxylate. Does this help?

I think you've made a mistake as that's citric acid being decarboxylated, and I'm not sure what that has to with the post.
You may have wanted to add in this citation: J. Phys. Chem., 1928, 32 (7), pp 961–981 DOI: 10.1021/j150289a001

As for the proposed reaction, it seems viable if you have a non-nucleophilic base to mop up the produced acid. Triethylamine, Hunig's base, etc. You should check the pKa's of the alpha carbons and tailor your base strength appropriately.

[Edited on 8-12-2014 by Chemosynthesis]
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[*] posted on 15-12-2014 at 13:43


Chemosynthesis,

Not clear what the petitioner is trying to do. He isn't telling us exactly.

Doubtful that he is actually trying to make acetone. But, if he is, it is probably easier to do it with acetone dicarboxylic acid, than with dihydroxyacetone.

Tell us more, Keftedes89.



[Edited on 15-12-2014 by zed]

[Edited on 15-12-2014 by zed]
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[*] posted on 16-12-2014 at 12:12


Quote: Originally posted by forgottenpassword  
I don't see why not. Solubility may be an issue. And pyridine isn't exactly harmless (if you're a male).


Where is the pyridine?




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[*] posted on 16-12-2014 at 14:48


Quote: Originally posted by vmelkon  
Quote: Originally posted by forgottenpassword  
I don't see why not. Solubility may be an issue. And pyridine isn't exactly harmless (if you're a male).


Where is the pyridine?

It's under the 'reaction arrow', as the solvent. Wouldn't pyridine be able to 'mop up', as proposed?
I agree on suspicious-ness, as the poster is worried about toxicity.




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