The Vespiary

The Hive => Methods Discourse => Topic started by: FriendlyFinger on December 05, 2002, 07:50:00 PM

Title: Oxalic or formic for Allyl alcohol?
Post by: FriendlyFinger on December 05, 2002, 07:50:00 PM

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.

Title: Oh? Where can the glycerol/formic acid procedure ...
Post by: Rhodium on December 05, 2002, 08:17:00 PM

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.

Title: Organic Synthesis Collectives Vol 1
Post by: FriendlyFinger on December 05, 2002, 08:50:00 PM

Rhodium,

The Formic/Glycerol method is here;

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

Regards,
FF

Title: Thanks, I added that one to the document.
Post by: Rhodium on December 05, 2002, 09:40:00 PM

Thanks, I added that one to the document.