Organic synthesis question(s)

[Sapps]

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How would I go about getting from a benzene ring to 3-chlorophenol? How do I even get a hydroxyl on the ring?

Also, using phenol and chlorobenzene, is there is a way to make diphenyl ether? Is this some kind of williamson synthesis?

 

[aug14]

How would I go about getting from a benzene ring to 3-chlorophenol? How do I even get a hydroxyl on the ring?

1. HNO3/H2SO4
2. Cl2, ALcl3
3a. Fe, HCl
3b. OH-
4. NaNO2, HCL
5. H3O+


Was this question on a mcat practice?

 

[Duran^2]

You can nitrate the aromatic ring and then reduce the nitro group to an amino group, then form the salt (maybe look up arenediazodium salts in your textbook) and from there you can make a phenol (adding an acid I believe). But the OH group is activating ortho and para and it looks like you need meta. Perhaps make nitrobenzene which would be meta-directing, stick on the chlorine, and then reduce the nitro to a hydroxyl group. But i'm not good at orgo, so take all of this with a grain of (arendiazodium) salt.

oops someone answered before me... looks like what i was getting at though.

 

[grw0o]

I hate organic, give me a circuit to analize anyday 👍 😛

 

[MDtoBe777]

Yea..I think you can get diphenyl ether from phenol and choloro benzene. The O would attack the carbon containing the chlorine. Chlorine would be displaced since it is a good leaving group. Then you just need a base to deprotonate the O. And then you get diphenyl ether (I think!).