November 01, 2024, 03:32:34 AM
Forum Rules: Read This Before Posting


Topic: Extraction technique and product isolation  (Read 3320 times)

0 Members and 1 Guest are viewing this topic.

Offline whawhaxd

  • Regular Member
  • ***
  • Posts: 14
  • Mole Snacks: +1/-0
Extraction technique and product isolation
« on: April 23, 2009, 12:43:43 PM »
I ran a reaction using THF as solvent. Can I use ethyl acetate for extraction to get my product out?
One of my friends told me to try this, but it doesn't seem to make sense because both are organic and
I wouldn't get two layers, would I?

Also, in terms of product isolation,

is it possible to obtain very viscous compound as my product? or how do I make it solid...?

Thank you!

Offline azmanam

  • Chemist
  • Sr. Member
  • *
  • Posts: 1416
  • Mole Snacks: +160/-24
  • Mediocrity is a handrail -Charles Louis d'Secondat
Re: Extraction technique and product isolation
« Reply #1 on: April 23, 2009, 12:56:03 PM »
Quote
I ran a reaction using THF as solvent. Can I use ethyl acetate for extraction to get my product out?

yes.  You'll probably quench the reaction by adding some aqueous acid or base or some such thing.  This will create a biphasic mixture: crude material in THF, water-soluble byproducts in water.  You'll separate them in the sep funnel, and put the aqueous layer back in the sep funnel.  Then you'll extract the aqueous layer with EtOAc.  You're extracting trace product out of the aqueous layer using an organic solvent, and EtOAc is usually just fine.  The only time it might be a problem is if you're quenching the reaction with strong acid or strong base.  You're likely to hydrolyze the ester and produce acetic acid - which may be detrimental to your system, and at the least has a much higher boiling point than EtOAc.

Yes, oils of all viscosities are quite common in organic synthesis.  Don't worry too much about making it a solid.  Just note that it's a viscous oil and move on.
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline Squirmy

  • Full Member
  • ****
  • Posts: 199
  • Mole Snacks: +24/-7
Re: Extraction technique and product isolation
« Reply #2 on: April 23, 2009, 07:08:42 PM »
It's worth mentioning that THF is miscible with water. (if you combine the two, they do not form layers).

If you workup a reaction run in THF with an aqueous solution, most of the THF will go into the aqueous layer. You can usually get away with directly extracting the mix of water/product/THF with EtOAc or some other solvent that isn't miscible with water.

However, having THF in the aqueous layer can change the partitioning of your product between the layers...i.e. the product becomes more soluble in the "aqueous" layer. In those situations, it may be necessary to remove the THF by distillation/rotavap before extraction.

Offline Med90

  • Regular Member
  • ***
  • Posts: 53
  • Mole Snacks: +2/-0
Re: Extraction technique and product isolation
« Reply #3 on: April 24, 2009, 11:30:25 AM »
yes, there will be no biphasic in the condition you have mentioned. It's better you first evaporate THF in rotary evaporator then extract your reaction mixture with EtOAc or other suitable organic solvents followed by washing with water, satd. NaCl and drying over MgSO4.
I hope this will work.
<a href="http://www.medchemblog.blogspot.com">medchem</a>


Offline azmanam

  • Chemist
  • Sr. Member
  • *
  • Posts: 1416
  • Mole Snacks: +160/-24
  • Mediocrity is a handrail -Charles Louis d'Secondat
Re: Extraction technique and product isolation
« Reply #4 on: April 24, 2009, 11:33:31 AM »
eh.  I've done reactions in THF.  Quenched with sat'd ammonium chloride poured into a sep funnel, washed with a bit of EtOAc (or Et2O) and get 2 layers just fine.  Maybe if you quenched with DI water... but a saturated salt should give 2 layers.
Knowing why you got a question wrong is better than knowing that you got a question right.

Sponsored Links