Sciencemadness Discussion Board

3,4-methylenedioxybenzoic acid to 3,4-methylenedioxybenzene?

ChemistryGhost - 14-1-2013 at 12:31

Hi. I wonder if there's anything on this. Maybe a decarboxylation would work. Any articles? Thoughts? I know you can just get 3,4-methylenedioxybenzene from catechol, but I want to know if there's a way to get there from 3,4-methylenedioxybenzoic acid. :cool:

kristofvagyok - 14-1-2013 at 13:15

Your signature there is a really important thing: "Imagination is more important than knowledge" ~Einstein"

In this case you have very-very limited knowledge from what do you want to do, mainly because there is absolutely no 3,4-methylenedioxybenzene existing. There is methylenedioxybenzene, also described as 1,2-methylenedioxybenzene, but not 3,4-methylenedioxybenzene.

And yes, it could be made easily by mixing it with sodium-hydroxide and dry distill it, also called decarboxylation. Search for "benzene from benzoic acid".

Organikum - 14-1-2013 at 15:16

Quote: Originally posted by kristofvagyok  
Your signature there is a really important thing: "Imagination is more important than knowledge" ~Einstein"

In this case you have very-very limited knowledge from what do you want to do, mainly because there is absolutely no 3,4-methylenedioxybenzene existing. There is methylenedioxybenzene, also described as 1,2-methylenedioxybenzene, but not 3,4-methylenedioxybenzene.

And yes, it could be made easily by mixing it with sodium-hydroxide and dry distill it, also called decarboxylation. Search for "benzene from benzoic acid".


I was always under the impression that the MD bridge wont stand such a treatment. But if it does, then it might survive the dry distillation of MD-phenylacetic acid with lead acetate (or iron) too, vacuum and inert gas flow is understood. This was declared to be impossible though I dont think anybody ever tried it. What do you think?

/ORG

kristofvagyok - 14-1-2013 at 16:16

Quote: Originally posted by Organikum  
I was always under the impression that the MD bridge wont stand such a treatment. What do you think?

/ORG

I've done a few aromatic decarboxylations and I have really good experiences with them. I have never worked with methylenedioxy compounds under those conditions but ethylenedioxy bridge always survived the decarb.(:

Also a really good method what I often use: dissolve 2eqv. potassium hydroxide in glycerol, heat it up to boiling point and add the carboxylic acid/ester/amide in small portions, reflux for 2hours, pour it on water, extract with ether and be happy with the product.