Guiafenesin

[Aurelius]

What would happen to this compound upon Claissen Rearrangment?  the possibility of a usable compound from gakk sparked my interest.

Post 414593 (missing)

(badbody: "Guaifenesin", Stimulants)

[Rhodium]

You can only perform Claisen Rearrangements on allylic ethers. Guaifenesin has no aliphatic double bond anywhere, so it won't react that way.

[Aurelius]

Dehydration.

[Rhodium]

Well, in the case it was first dehydrated to the allyl ether, the major product would be 2-hydroxy-3-methoxy-allylbenzene (I doubt that would be usable) and the minor product would be eugenol...

[Aurelius]

It was worth a shot.  I just looked at that molecule and said " hey, it'd be great if they handed us precursors."  But alas, it was not to be. 

oh well.