Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: CinnabarCherry on April 06, 2022, 04:02:03 PM
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Hi all,
I'm planning to set up an oxidation of an indoline to a 1H-indole. The procedure am following uses DDQ in 1,4-dioxane followed by quenching with saturated NaHCO3, which seems standard for this reaction.
Why is 1,4-dioxane used as the solvent and how does the bicarb quench the reaction. Thanks!
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Some information https://en.m.wikipedia.org/wiki/2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
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DDQ is reduced to the corresponding phenol and this is a bit acidic so you wash it away with NaHCO3. You can use many solvents, dioxane is not special.
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Much appreciate everyone. It sounds like hydroquinone is insoluble in dioxane which facilitates the reaction.