Catechol tailing on TLC

[emyonee]

Hello I'm trying to synthesis a product (which is more polar) from catechol. The problem is catechol (dissolved in methanol) always tails when I spot it on a silica TLC plate. With this I won't be able to tell if there was any product formed in the reaction. I have tried increase the polarity of the mobile phase and reduced the concentration of catechol but still same thing. What can I do to stop the taling? Thanks.

[Fuzzwood]

Perhaps a drop of acid to keep the catechol protonated.

[hypervalent_iodine]

Hello I'm trying to synthesis a product (which is more polar) from catechol. The problem is catechol (dissolved in methanol) always tails when I spot it on a silica TLC plate. With this I won't be able to tell if there was any product formed in the reaction. I have tried increase the polarity of the mobile phase and reduced the concentration of catechol but still same thing. What can I do to stop the taling? Thanks.

 

What is your product? Even with tailing, and assuming you've properly optimised your running solvent, you should still be able to see a product spot. The real issue comes with separation on a silica column.

 

Otherwise, a good trick is to pre-treat your plate with your solvent plus 2-5% TEA and subsequently run your spot in your solvent plus about 1% TEA.