[alis88]

How do you remove a =O group from a ring compound, e.g. hexanone?

[kui]

maybe clemensen reduction

amalgamed zinc + conc. HCl + heat

[nielsgeode]

For clemmensen you need mercury 

You can also make a thioketal with HSCH2CH2SH and then hydrogenate that by bubbling H2 in the presence of a Pd catalyst

[nj_bartel]

(amalgamed)

[macman104]

Or Wolff-Kishner reduction as well.

[alis88]

Thank you so much.

I have looked into the Clemmensen reaction.

For the attached reaction, is the Clemmensen reaction all that is needed to convert the first compound into the other?

[russellm72]

The Clemmenson and Wolf Kischner reductions are pretty harsh conditions and have no idea how the aliphatic framework would survive. I suggest you go for a milder method using the thioacetal or a hydride reduction of a suitable hydrazone. I would suggest an even better method would be the Barton reduction of the derived Xanthate. They are easy to make and conditions are mild.

p.s. If you are just doing this as a theroretical excercise then the early methods all stand up fine. Of course in practice things are much different.

Good luck

[alis88]

Thanks a lot.

Yes, I am just looking for a theoretical solution.

Would the Clemmenson reaction work for the above reaction then? I am unsure as to what would happen to the other rings and the OH group.

Could someone please explain?

[sjb]

I can't see any theoretical reason why not, maybe the phenolic OH is a touch acidic, so might interfere? I note you've drawn the second structure with stereochemistry at the bottom 6-6 ring junction, but the precursor does not has this - merely an oversight, or are you not sure about this?

[alexjaco]

Just another idea...reduce it, convert it to a good leaving group (ex OTs) then hit it with super hydride to displace with a hydride.  There really is no good way to do it in one step, as mentioned, the one steppers are very harsh conditions.

[alis88]

sjb - I am unsure about that. I am wondering if the stereochemistry of the molecule changes.

Thank you everyone for your help.

[Doom91]

dear Russelllm72
what do you mean by the aliphatic framework would not survive under clemmenson and wolff kishner reduction