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Topic: What is DDQ  (Read 1683 times)

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Offline CinnabarCherry

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What is DDQ
« 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!
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Offline Hunter2

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Re: What is DDQ
« Reply #1 on: April 06, 2022, 04:12:31 PM »
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Offline rolnor

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Re: What is DDQ
« Reply #2 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.
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Offline CinnabarCherry

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Re: What is DDQ
« Reply #3 on: April 07, 2022, 03:45:41 PM »
Much appreciate everyone. It sounds like hydroquinone is insoluble in dioxane which facilitates the reaction.
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