FriendlyFinger (Hive Bee)
12-05-02 19:50
No 386691
      Oxalic or formic for Allyl alcohol?  Bookmark   

Hi there,

I've been dabling with the Formic/Glycerol method for Allyl alcohol, and having problems. When I read about yields from both Oxalic and Formic they seem about the same. They both seem to take a fair amount of time. Is one much more prefered than the other. I notice that Rhodium has only the Oxalic method on his/her site.

Regards,
FF.
 
 
 
 
    Rhodium
(Chief Bee)
12-05-02 20:17
No 386698
      Oh? Where can the glycerol/formic acid procedure ...  Bookmark   

Oh? Where can the glycerol/formic acid procedure be found?

When heated, glycerol reacts with oxalic acid to form the ester glyceryl oxalate, which upon further heating decomposes to CO2 and glyceryl formate (the formic acid ester), and this then in turn dehydrates to allyl alcohol.

So - if formic acid is just as easy for you to aquire as oxalic acid, then by all means go for formic acid directly, and save yourself a potentially yield-lowering step.
 
 
 
 
    FriendlyFinger
(Hive Bee)
12-05-02 20:50
No 386702
      Organic Synthesis Collectives Vol 1  Bookmark   

Rhodium,

The Formic/Glycerol method is here;

Kamm, O. Organic Synthesis Collectives Vol 1 page 25-43.

Regards,
FF
 
 
 
 
    Rhodium
(Chief Bee)
12-05-02 21:40
No 386721
      Thanks, I added that one to the document.  Bookmark   

Thanks, I added that one to the document.