[metallica00789]

Hi,
I am synthesizing 4-bromoacetanilide using the following reaction:

I need to purify the product by dissolving and re-crystallize it. I need to use a solvent that will dissolve 4-bromoacetanilide only at high temperatures. I am thinking  of using an alcohol with a long r chain, like propanol or butanol, since 4-bromoacetanilide has a polar components (acetate, and amine). Do you think that long chained alcohols will do the job?
Thank you.

[Dan]

Check the literature, this recryst will have been done before. It is very difficult to predict the best solvent from the structure, you have to do some experiments.

[OC pro]

Do an acidic work-up using KHSO4 and ethyl acetate. The aniline will go into the aqueous layer and your product will go into the organic layer. This is simple acid-base extraction. I recognize you are carrying out synthesis without knowing the very basics of organic chemistry. After careful extraction, your product will be >95% pure. Recrystallization should work with ethanol or ethanol/water mixtures.

[OC pro]

Btw: have you tried google before? There are tons of manuscripts describing the synthesis of your compound. Use ethanol for recrystallization (as suggested from me before).

[metallica00789]

Do an acidic work-up using KHSO4 and ethyl acetate. The aniline will go into the aqueous layer and your product will go into the organic layer. This is simple acid-base extraction. I recognize you are carrying out synthesis without knowing the very basics of organic chemistry. After careful extraction, your product will be >95% pure. Recrystallization should work with ethanol or ethanol/water mixtures.

I am still a student, but I know the very basics I am not allowed to do acid-base extraction in this experiment.

[OC pro]

Then you should have mentioned that you are not allowed to do acid-base washing. That clears things up. But aqeuous work-up is allowed?

[OC pro]

The problem is: if you have a very dirty mixture recrystallization will not improve the quality of your material. Very often, material has to be pre-purified before recrystallization. Thats why I suggested acid-base extraction.
Why is acid-base not allowed? It seems stupid to me...

[opsomath]

Is this in a class? If you do the reaction carefully, after aqueous workup you will have nearly a pure compound. Acid workup is nice in this case, but not strictly necessary. Ethanol is very likely to be a good recryst solvent for you.