Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sharbeldam on June 22, 2021, 03:34:04 AM

Title: Extraction
Post by: sharbeldam on June 22, 2021, 03:34:04 AM
I need to separate these 4 by extraction, I don’t work in a lab but I was wondering if this way would be possible. First I’d use a weak base to ionize the carboxylic acid to make it go to the aqueous phase and separate , then use a strong base to ionize the phenol and separate, but I’m left with two that I don’t know what to do (using extraction by solvents not form complexes) , how would I separate them? If I use a strong acid to ionize methylpyridine then it would also hydrolyze the ester.

Any ideas? Ty
Title: Re: Extraction
Post by: sjb on June 22, 2021, 04:55:01 AM
Cc1ccncc1C[C@@H]1CCC[C@@H]1C(=O)O COC(=O)C1CCCC1CC1=CC(=CC=C1)O

Good thinking so far. In reality, the protonation of the 4-methylpyridine will be much faster than the hydrolysis of the ester so you have a chance there. I'm not sure if you need a strong acid to do this. Alternatively, I've extracted pyridines with copper sulfate before, and I don't think that would affect the ester?
Title: Re: Extraction
Post by: sharbeldam on June 22, 2021, 05:10:05 AM
thank you, basically two ways
1) CuSO4
2) using a moderate acid so it wont touch the ester but protonate the pyridine ring.

if i may ask, can you tell me what happens with CuSO4 and pyridine exactly? tried to look it up, didnt find any, would it form like a solid complex that i can filtrate or?
Title: Re: Extraction
Post by: rolnor on June 22, 2021, 06:20:46 AM
You can probably use acetic acid for the pyridine
Title: Re: Extraction
Post by: Babcock_Hall on June 22, 2021, 12:21:44 PM

This is an interesting thread on removal of pyridine.  The complex with cupric ion is not a solid IIRC.