The Vespiary

The Hive => Chemistry Discourse => Topic started by: Aurelius on July 14, 2003, 11:18:00 AM

Title: Guiafenesin
Post by: Aurelius on July 14, 2003, 11:18:00 AM

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)

Title: Guaifenesin doesn't do Claisen Rearrangements
Post by: Rhodium on July 14, 2003, 04:59:00 PM

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

Title: Rhodium
Post by: Aurelius on July 14, 2003, 07:04:00 PM

Dehydration.

Title: Dehydration followed by Claisen
Post by: Rhodium on July 15, 2003, 07:13:00 AM

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...

Title: Thanks
Post by: Aurelius on July 15, 2003, 07:18:00 AM

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.