Re: ORGLIST: Purification of 2,5- Dimethoxyaniline

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From: Jack Sullivan (jsulliva$##$
Date: Sat May 16 1998 - 01:49:58 EDT

jchubb$##$ wrote:
> I am a chemistry student and am currently trying to do some organic
> synthesis. I wish to purify my 2,5-Dimetoxyaniline as it appears to me
> that my compound has been partially oxidised. Iwould greatly appreciate
> if anybody can give me some information(/reference) regarding the above
> matter.
> Hope to get assistance as soon as possible.
> Thank you
> Barnabas
> ______________________________________________________
> I would think that you could form the hydrochloride salt of the desired
> aniline and recrystallize it away from the oxidation product.
> I would expect the first oxidation to occure at the nitrogen, to make
> 1-nitro-2,5-dimethoxybenzene. This would not form a hydrochloride salt and
> should be fairly soluable in organic solvents.
> So, why do you want to clean up your 2,5-DMA? What are you planning on
> doing with the material?
> John Chubb, Ph.D.
> Quality Chemicals, Inc
> __________________
I worked with this product and puried industial material on a 50
pound-batch scale by recrystallizing from hot methanol. It was then let
crystallize via overnight cooling, centrifuged and washed with cold
methanol and then water. I worked with Tenn. Eastman material, which
does not appear to be available now. Purrication of the darker European
material by the same method gave inefrior product.

This material is a very air-sensitive generator of an unpleasant
dark-brown pigment that dyes most fabrics and surfaces with a
practically ibdelible brown stain. In its pure form it is a white
craysalline solid.

Jack Sullivan

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