[makkes]

Best chemist,

I'm currently doing research to self-healing polymers at NovAM (TU Delft). The reaction I did was a conversion of a di-ester (diethyl malonate) to a di-alcohol with AlLiH4 as catalyst (in THF). During my reaction (after 24h) I took a TLC and I saw 1 concentrated spot and 2 very small spots who were hard to see. I decided to work-up my reaction by quenching with water follows by the addition of 10% H2SO4 to dissolve the salts. After extraction I took another TLC and saw 2 bright spots and the two small spots. I'am really wondering what the second bright spot could be and I hope that someone can tell me what it could be.



This reaction is used to be a simple reaction, because ethanol is the only by-product. LAH is the strongest catalyst for this reaction, so I don't understand why there is a second product in nearly the same concentration as the major product.

I hope you can help me out!

Max Wempe

[phth]

What is a catalyst: something consumed or preserved after a reaction?

[OrganicDan96]

have you got an NMR, what is the structure?, I have heard of LiAlH4 reductions failing due to Li coordinating with the molecule (such is true with crown ethers), if possible you could consider using diisobutyl aluminium hydride in excess.

[clarkstill]

I guess you might also worry about E1cb elimination of the beta-hydroxy ester intermediate? Or retro-aldol to give ethyl acetate and formaldehyde?