I've got a tutorial question that asks,
"Describe two methods for the following conversion:
4-formylcyclohexanone -> 4-methylcyclohexanone"
- Since the aldehyde is more reactive than the carbonyl, perhaps protect the aldehyde with ethane-1,2-thiol, then protect the ketone with 1,2-ethanediol, then reduce the protected aldehyde (the diothiolane) to CH3 by H2 over Raney Nickel...then deprotect the ketone with acid.
Can I selectively protect the aldehyde, or would both the ketone and aldehyde be protected by the diothiol?
Is the method I have given reasonable?
Here is the reaction scheme of the first method:
I've had some trouble thinking of a second method. This article http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0289
says, Clemmenson reduction "is not particularly effective, however, with alicyclic and aliphatic ketones".
So would Zn(Hg) in HCl reduce the aldehyde to the alkane without affecting the cyclic ketone?
Or would the Wolff-Kishner reduction?