[Topi]

Hi,
can someone help with the reaction from a benzene to a 1-metyl-4-chlorcyclohexane.
I need the intermediate steps and the reagents at each step.

thanks,

[Yggdrasil]

Please read the Forum Rules[/url].  We require that you post your attempts to solve the problem before we will help you.  Also, for clarification, is your starting material benzene or cyclohexene?

[Topi]

benzene, sorry bout that..

I cant see how we get rid of the double bound. Maybe addition of H2 in one step, then addition of Cl, but i cant see hoe to add a methyl group.

[Yggdrasil]

You would probably need to add the methyl group prior to reducing the aromatic ring.  For reduction, you might want to try looking at a Birch reduction.   However, I'm not completely sure I know how to solve this problem, so these are just suggestions and I'm not sure that they are on the right track.

Good luck.

[Topi]

anyone?

[Topi]

dont know how to post image..but i can email it?

[sjb]

If you click on "additional options", below, you will see a box to upload an image...

If you're certain it's 1-methyl-4-chlorocyclohexane you want, does it matter if it's cis or trans?

[Topi]

image:
as you see, its a  three step reaction

[refid]

is it possible to do EAS (methylate & chlorinate) then catalytic hydrogen to reduce the benzene to cyclohexane?

[kiwi]

those would be my thoughts, benzene -> toluene -> p-chlorotoluene -> product. you should be able to think of reactants for those steps (at least the first two, http://en.wikipedia.org/wiki/Hydrogenation will help for the last)

[sjb]

those would be my thoughts, benzene -> toluene -> p-chlorotoluene -> product. you should be able to think of reactants for those steps (at least the first two, http://en.wikipedia.org/wiki/Hydrogenation will help for the last)

Yeah, thought about that, my only concern was that most reagents I know about for the hydrogenation are fairly harsh and would probably reduce the C-Cl bond back to a C-H; unless things have moved on since last time I rambled through the lit.

S

[kiwi]

yeah i have my concerns too, and would worry about this route in practice. but this will work on paper