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Purifying an aromatic glycoside from tetrabutylammonium ion

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Babcock_Hall:
We checked the fractions with reverse phase TLC, and we mainly detected with UV light.  PMA stains the whole plate, if I recall correctly.  There is no amine, but there is a vinyl group present.  There is a chance that KMnO4 would work as a stain.

I think that the acid may come from Dowex-50 in the Kaburagi-Kishi technique of removing the TBA ions.  Perhaps adding a greater proportion of CaCO3 relative to Dowex-50 would buffer this.

rolnor:
KMnO4 will react with the carbon in the C-18 but initially the vinyl will stain, it reacts faster.

rolnor:
There is anisaldehyde/H2SO4/MeOH i think, that stains almost anything, it could work.

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