psycosmo (Newbee)
12-23-01 14:44
No 250110
      3,4,5 trimethoxy phenylacetic(or propinoic) acid  Bookmark   

I had an Idea about how to make 3,4,5 phenyl acetic or phenyl propinoic acid from eugenol.

1) Treat Methyleugenol with KMnO4 (for the acetic acid) or H20, H202 and NaOH then KMnO4 (for the propinoic acid)

2) Now since that COOH is meta- directing chlorination or bromination of the benzene ring with, say FeCl3 and Br2 should should set us up for 3,4,5 trimethoxy formation.

3) To do this, treat with NaOh, then MeI, which I think should form the 3rd methoxy group.

Where one would go from this I don't know, forming amides from carboxylic acids seems to be either highly toxic (such as the thionyl chloride method) or highly ineffecient (heating with ammonia method).
(Hive Addict)
12-23-01 18:45
No 250145
      Re: 3,4,5 trimethoxy phenylacetic(or propinoic) acid  Bookmark   

Urea readily donates an amide group to carboxyls, itself then decomposing to amonia gas and carbon dioxide.

Urea is carbamide: (NH2)C=O


Vivent Longtemps la Ruche!
(Chief Bee)
12-25-01 12:15
No 250411
      Re: 3,4,5 trimethoxy phenylacetic(or propinoic) acid  Bookmark   

Only COOH directly attached to the ring is meta-directing, not if it is a phenylacetic or phenylpropionic acid. You would get ortho-substitution with the bromine next to the side chain.