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?
forgottenpassword - 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).zed - 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?
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]zed - 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]vmelkon - 16-12-2014 at 12:12
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.
