I would like to attach a carbon triple bond to a benzaldehyde ring and to do that i am trying to perform a williamson reaction: https://en.wikipedia.org/wiki/Williamson_ether_synthesis.
The two OH groups on my ring should turn into ethers, by making them react with a propargyl halide, in the presence of a salt, in my case, potassium carbonate. At the moment of extracting i have used ethyl acetate and water and i think it pretty much worked, at least to remove the salt. What was hard was to find a good combination of solvents that could return a visible separation on the TLC plates and that could also dissolve my product! I have tried various ratios of hexane and ethyl acetate but either i was not dissolving the product or it was not working on the TLC. Is this a frequent obstacle? How can I approach it? Thank you!
I think you can approach the problem of selecting the optimal combination of solvents through Statistical Designed Experiments, particularly involving Mixture Designs Setup and Multi-objective Optimization through sequential exploration and Analysis of your System response surface behavior.
The following texts contain extensive coverage of the Topics mentioned above :
1) Applied Regression Analysis : Draper and Smith
2) Response Surface Optimization: Myers, Montogomery and Cook
3) Chemometrics | Experimental Design : Ed Morgan.
What is the stationary phase of TLC? Silica gel? Try maybe THF or DCM:MeOH. 95:5.
Regards
G
Grzegorz Boczkaj aren't both DCM and MeOH polar? This way I wouldn't see any separation on the silica
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