Sciencemadness Discussion Board

benzilic acid ethyl ether=benzilic acid ethyl ester?

xionoland - 18-6-2011 at 15:11

Hello. I need (benzilic acid ethyl ether) m.p. 114C for a synthesis but I only find information on (benzilic acid ethyl ester) on net... Is that another chemical or is it the same chemical/ typed wrong in the synthesis?

UKnowNotWatUDo - 18-6-2011 at 15:51

Benzilic acid has two hydroxyl groups which can be bonded to an ethyl group. One is part of it's carboxylic acid group. An ethyl group attached here would make it an *ester*. Hence benzilic acid ethyl ester. The second hydroxyl group is attached to the quaternary carbon atom and is an alcohol. An ethyl group attached here would make it an *ether*. Hence benzilic acid ethyl ether.

xionoland - 18-6-2011 at 16:00

thanks, but there is some more information in this synthesis that I find a bit hard to understand.

"benzilic acid ethyl ether was boiled in 100ml acetone with 20g of potassium carbonate and 13g of 2-(dimethylamino)-ethyl chloride for 24h on a water bath. The acetone was distilled off and the residue partitioned between ether and water"

Does that mean boil this chemical with a reflux apparatus heated on a boiling water bath for 24h, then evaporate the acetone? Or just boil off the acetone and let the rest be warmed for 24h?

not_important - 18-6-2011 at 17:03

The Rhodium page you're quoting from clearly shows that this is the ethyl ether. Technical instructions are in effect step-by-step descriptions of what to do, generally assuming that you have sufficient experience to comprehend them ("those knowledgeable in the art") It's very simple and clear - heat for 24, then distill the solvent away. But first get some practical chemistry experience and knowhow, so we don't have to read your obit too soon.

Nicodem - 19-6-2011 at 01:09

This thread reeks of "RC chemicals" business, but since it appears like nature itself is about to take its action to restore the equilibrium, I'll let it be.
Quote: Originally posted by xionoland  
thanks, but there is some more information in this synthesis that I find a bit hard to understand.

"benzilic acid ethyl ether was boiled in 100ml acetone with 20g of potassium carbonate and 13g of 2-(dimethylamino)-ethyl chloride for 24h on a water bath. The acetone was distilled off and the residue partitioned between ether and water"

Does that mean boil this chemical with a reflux apparatus heated on a boiling water bath for 24h, then evaporate the acetone? Or just boil off the acetone and let the rest be warmed for 24h?

So you have no clue of chemical nomenclature, don't comprehend the theoretical aspects of the chemical transformations and don't understand even as simple instructions as the quoted one. Yet you already want to work with a nitrogen mustard! Must be evolution in action, I guess. Good luck.

If I were you, I would check the original references, rather than trust the copy-paste reliability of the Rhodium archive.

PS: Beginner and referenceless threads are to be opened only in the Beginnings section, where this one is being moved.