[Thalidomide]

Hi everyone! First-time poster here, although I've lurked every now and then for the last few weeks. I'll introduce myself properly at some point, but for now all everyone needs to know is that I'm a final year undergrad doing a honors project in O. chem Anyway...

Some time ago, I attempted to make diethyl squarate (5231-87-8) from squaric acid (2892-51-5). The procedure involved ethanol, trimethylorthoformate (to get rid of pesky H2O), and a lot of refluxing. Diethyl squarate is supposed to be a yellow liquid. I was ending up with pasty/solid beige gunk. Epic fail.

I put the RBF aside and temporarily gave up on it so that I could focus on other reactions instead (we still had a bit of old diethyl squarate left over in the lab, afterall, so I didn't really see it as a priotity) and didn't think of it again until today, when I spotted the RBF in the corner while cleaning.

"Well, this never worked out" I thought as I picked up the RBF, uncapped it, and proceeded to throw it out...only the gunk had solidified and wouldn't dissolve immediately. I then filled it with tap water and let it sit in the fumehood until it dissolved. It is water soluble, so it didn't take too long. Before I could pour it out, however, I had to go to a group meeting.

...where I was told that physical appearance doesn't always matter, and that I should try other things and take some NMRs of the beige gunk I did have. I put on my best *Ignore me, I am dishonest* face and nodded at the idea of taking an NMR.

This is where I need help: how do I extract the product I have dissolved in tap water there before my supervisor finds out what happened?   I don't really want to just stick it on the rotavap and crank the heat since it will take forever (there's a lot of water). I'm also kind of scared to experiment with a bunch of random organic solvents since I have no idea what the beige gunk was (I'm assuming I had mostly squaric acid and a bit of diethyl squarate?) and therefore have no idea what solvent will actually draw it into the organic phase. It did dissolve rather easily in water...does anyone have any ideas?

Or should I re-do it entirely after saying that "the product got lost"?

Any info will be appreciated  

[MissPhosgene]

Try ethyl acetate to get the diethyl squarate out. You will probably get some squaric acid out as well. Try acidifying the water layer a little and then re-extract with ethyl acetate to get even more squaric acid. Don't acidify until after you are finished trying to get diethyl squarate out of the water.

The crude NMR idea is a really good one, by the way.

Or, just try it again. You may end up needing to anyhow.