Print Page - Simple question (curiosity)

Title: Simple question (curiosity)
Post by: Jubrail on July 05, 2003, 05:59:00 AM

This is an orgo. theory question:

If I have a benzene ring with NH2 attached and want to replace this with COOH:

_ _
/ \_NH2 --> / \_COOH
\_/ \_/

I believe that the text book way to do this is to convert the molecule to a disulfide salt with NaNO2 and HCl, then use Cupric Cyanide / Potassium CN to change it into a benzen ring with a CN on it. Then it can be reacted in an acidic aqueous solution to get the desired molecule.

First off, is this correct? Secondly, is there another route that can be used?

No, I am not a college orgo student, that needs help on his homework. I am an ignorant man trying to teach myself some chemistry.

Title: 1. NaNO2/H(+) ----> diazonium compound 2.
Post by: Osmium on July 05, 2003, 06:42:00 AM

1. NaNO2/H(+) ----> diazonium compound
2. React with CuCN ----> benzonitrile
3. hydrolyse to produce the acid

Title: Thanks, Os
Post by: Jubrail on July 05, 2003, 07:35:00 AM

But my question was if that was the only path to the final compound?

Title: the one pot low yield method
Post by: acid_egg on July 05, 2003, 07:45:00 AM

http://www.chem.leeds.ac.uk/delights/texts/Demonstration_09.htm (http://www.chem.leeds.ac.uk/delights/texts/Demonstration_09.htm)

...and you may have some problems retrieving the product. :P

Title: Thanks
Post by: Jubrail on July 05, 2003, 08:13:00 AM

Definitely appreciated. I can now sleep at night.

The Vespiary

The Hive => Chemistry Discourse => Topic started by: Jubrail on July 05, 2003, 05:59:00 AM