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Author: Subject: 1-amino-2-propanol
Nicodem
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[*] posted on 13-5-2008 at 22:02


Using NaOCl on propylene should give propylene oxide directly since the intermediate chlorohydrine cyclisizes to the epoxide in basic media. The preparation of 1-chloro-2-propanol from propylene glycol was already discussed on this forum in a thread about 2-chloroethanol preparation (there are some references there).
Also, both regioisomeric halohydrines derived from propylene give the same aminoalcohol if used in the reaction with ammonia since the first step is always the cyclisation to propylene oxide. So it does not matter if you use 1-chloro-2-propanol, 2-chloro-1-propanol or propylene oxide, the product in nucleophilic substitutions is always the same. A normal SN2 on 1,2-halohydrines is not possible due to the neighboring group participation(cyclisation to an epoxide followed by an SN2 on the epoxide ring; thus leading to retention of configuration). A similar neighboring group participation is observed in alpha-halo-carboxylic acids (for example the reaction of 2-chloropropanoic acid with amines, etc.).




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MagicJigPipe
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[*] posted on 13-5-2008 at 22:15


NaOCl on propylene, eh? That would be an interesting setup. Or perhaps just a simple "bubbling through" type setup (a la chlorine and toluene) would suffice. Then just distill...

Even though I doubt there would be information on this I will do a search tomorrow (it's late...)

Thanks for the information, Nicodem.




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S.C. Wack
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[*] posted on 14-5-2008 at 03:28


Quote:
Originally posted by MagicJigPipe
Surely, you are not in the US because I would have heard of this.


I'd make up the fact that I'm in Bumfuck, USA by choice? (I'd move to a wet spot of WA or OR if I could afford it). I sure go to a lot of trouble to use amerikan spellings. I traded my euros for dollars so I could post this picture featuring $1 coins that are keeping the bottle from rolling onto my lap.

A search of Ace using the magic word propylene gives the impression that they sell Matheson product in containers a little smaller than this one.

Propylene glycol would be a lot cheaper.

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MagicJigPipe
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[*] posted on 14-5-2008 at 10:15


I meant no offense by it. Ace must be the only place. I have not been to the solitary Ace Hardware in my area (~25miles). Thanks, though. I shall check this out.

I didn't notice that your info says you're in the US.

Also, I can get propylene glycol by the 5 gallon jug for ~$60. I hate that glycols are so expensive. Even ethylene glycol is $9 a gallon.

[Edited on 5-14-2008 by MagicJigPipe]




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mfilip62
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[*] posted on 16-12-2017 at 02:47


I would suggest propylene glycol and HaloAcetone as starting materials!

If polyols like PG follow the same chemistry as normal alcohols once could selectively
halogenate primary or secondary -OH (secodary maybe by using Lucas reagent than
do the Finkelstein reaction to replace Cl by I and react it with desired amine!

Other route would be reacting hydroxyacetone with Hydroxylamine followd by mild reduction
or reacting HaloAcetone with desired amine (with some catalyst like DIPEA/DIEA aka Hűgins base!) folowed by transforming =O into -OH!

Mixture of isomeres is not problem.
Once you halogenate remaining -OH group you can re-arrange the molecule by Aziridinium
mechanism.

Those are by far,most easyest way I can think of for producing some,at least one of the mentioned method SHOULD WORK! (I spend whole summer researching secondary and tartiary
halogenpropylamines)

;)
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