[jlee808]

Have this problem here hoping some of you could shine a lite into it.


I was thininking Birch reduction because that's the only thing about aromatic rings reduction that was in lecture but don't know how to reduce it totally  .
Thanks for any suggestion guys

[discodermolide]

Have this problem here hoping some of you could shine a lite into it.


I was thininking Birch reduction because that's the only thing about aromatic rings reduction that was in lecture but don't know how to reduce it totally  .
Thanks for any suggestion guys

Look up Nishimura's catalyst.

[jlee808]

Looked up Nishimura's not much info on google. Not in my book. I could see briefly that it reduce the aromatic ring down. but would it affect the Ome?

If I used Birch reduction and follow this:


What would I do next to get my product?

[discodermolide]

Looked up Nishimura's not much info on google. Not in my book. I could see briefly that it reduce the aromatic ring down. but would it affect the Ome?

If I used Birch reduction and follow this:


What would I do next to get my product?

3-methylanisole is commercially available. Nishimura's catalyst should not touch the methoxy group. Look at Houben-Weyl's volume on hydrogenation.

[Arctic-Nation]

I'm not sure you're being very helpful here, disco.

As long as this is a theoretical problem, I'd do something like demethylation (ether cleavage with HI or BBr3), followed by reduction to cyclohexanol over a rhodium catalyst, and then reoxidation to the ketone. Standard textbook reactions.

[discodermolide]

I'm not sure you're being very helpful here, disco.

As long as this is a theoretical problem, I'd do something like demethylation (ether cleavage with HI or BBr3), followed by reduction to cyclohexanol over a rhodium catalyst, and then reoxidation to the ketone. Standard textbook reactions.

The questioner asked about the total reduction of aromatic rings, Nishimura's catalyst is a mixture of rhodium on alumina and does the job.

[fledarmus]

Still needs a meta-methylation and an ether cleavage...

[discodermolide]

Still needs a meta-methylation and an ether cleavage...

He did not ask for that!

[orgopete]

I don't want to tip this off just yet, but since poster mentioned Birch reduction, this looks like a Birch reduction problem.

Hint, last step looks like a Gilman addition.