Hi everyone.
I hope you could help me solve this proble:
I am trying to obtain dibenzyl fumarate from fumaric acid and BnOH through Fischer esterification reaction. The problem comes by the use of sulfuric acid as catalyst, that polimerizes and oxidizes BnOH. Although the product is generated, the purification is quite complicated because of sideproducts. I've tried using DCC as acylating agent (with DMAP as catalyst) but same thing happens with sideproducts. The best synthesis i have done till now is acid transesterification of dimethyl fumarate with BnOH in presence of p-toluensulfonic acid. The latter works much better but i can't find a suitable purification method.
Thank you!
Dear Agustín Rojas,
The following info may turn out to be useful:
https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-fumarate
https://pubchem.ncbi.nlm.nih.gov/compound/Fumaric-acid
https://go.drugbank.com/drugs/DB01677
https://www.sigmaaldrich.com/US/en/product/aldrich/128422
Hello Agustín,
thank you for sharing this interesting chemical question with the RG community. I think that all these problems which are outlined in your question could be circumvented by employing a more reactive derivatives of fumaric acid such as fumaryl chloride, Cl-C(=O)-CH=CH-C(=O)-Cl. As an acid chloride this compound has a much higher reactivity towards alcohols than the free acid. The reaction can be facilitated by adding a base such as triethylamine to capture the HCl formed during the reaction. for a description oft his reaction please have a look at the following Open Access literature reference:
Novel Heme Oxygenase-1 (HO-1) Inducers Based on Dimethyl Fumarate Structure
(please see attahed pdf file)
Good luck with your work and best wishes, Frank Edelmann
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