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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: CinnabarCherry on April 06, 2022, 04:02:03 PM

Title: What is DDQ
Post by: CinnabarCherry on April 06, 2022, 04:02:03 PM

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!

Title: Re: What is DDQ
Post by: Hunter2 on April 06, 2022, 04:12:31 PM

Some information https://en.m.wikipedia.org/wiki/2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Title: Re: What is DDQ
Post by: rolnor on April 06, 2022, 11:12:55 PM

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.

Title: Re: What is DDQ
Post by: CinnabarCherry on April 07, 2022, 03:45:41 PM

Much appreciate everyone. It sounds like hydroquinone is insoluble in dioxane which facilitates the reaction.