[rleung]

Hi,

I am wondering if this synthesis works.  Thanks.

Ryan

[Albert]

I don't think so.
Mind you, do you need to synthesize the final product you drew from that derivative of cyclohexanone? Can't you start from a different compound?

[rleung]

Hi,

Nope, I have to start from the reagent I used and end up with the product I need.  If I convert the acyl chloride into an ester using SOCl2/CH3OH, that would be better, right?

Ryan

[Albert]

I sincerely doubt you can use NaOH as a base, because I think it'd react with the-CN group to yield a carboxylic acid.
If I were you, I'd choose NaH.

[movies]

Acid chlorides tend to acylate on the oxygen of an enolate in preference to the carbon atom of an enolate.

[netscape]

I'm afraid this synthesis won't work, even using NaH as base and an ester instead of acyl chloride.  I see two potential problems:

1) Regioselective issue:  There is really no real preference to which side of the cyclohexanone is going to be deprotonated.  They are equally substituted.

2) Use of a base to deprotonate the position you want may also lead to elimination of CN- to give an cyclohexenone.

You may get some product ,  but the yield will be low and it might be messy.