[chacocha]

Hello all,

I'm trying to figure out a synthesis route from benzene to the kevlar monomers, and it seems easy because there's two of the same functional groups but I'm not sure where to start.

So for benzene with 2 NH₂ groups, I guess I can start with NO₃/H₂SO₄ and put NO₂ on the ring, and repeat it so that I have 2 NO₂ groups attached to the ring. After that, can I use LiAlH₄/H₂o to reduce both NO₂ down to NH₂? But that would result in meta relationship, so would that still work?

For dicarboxylic acid, I'm thinking FC acylation first and then oxidizing it using KMnO₄, so that would give me one carboxylic acid on the ring. How can I add the second carboxylic acid?

[sjb]

Hello all,

I'm trying to figure out a synthesis route from benzene to the kevlar monomers, and it seems easy because there's two of the same functional groups but I'm not sure where to start.

So for benzene with 2 NH₂ groups, I guess I can start with NO₃/H₂SO₄ and put NO₂ on the ring, and repeat it so that I have 2 NO₂ groups attached to the ring. After that, can I use LiAlH₄/H₂O to reduce both NO₂ down to NH₂? But that would result in meta relationship, so would that still work?

For dicarboxylic acid, I'm thinking FC acylation first and then oxidizing it using KMnO₄, so that would give me one carboxylic acid on the ring. How can I add the second carboxylic acid?

Consider directing effects...

[chacocha]

Can you elaborate on that? I know that NO2 and carboxylic acid are both meta directing.

[chacocha]

I forgot to attach the picture of the monomers.

[kriggy]

Can you elaborate on that? I know that NO2 and carboxylic acid are both meta directing.

Yes they are so if you want to have them in para position, you should consider different approach.

[chacocha]

Ok. So should I put NO₂ first, reduce it down to NH₂ and then repeat it so that I would have NO2 in para position? And then I just reduce it again? Is that it?

For carboxylic acid, if I do F/C alkylation twice in a row so that I have two alkyl groups in para position and use KMnO₄, would that change both alkyl groups into carboxylic acids?