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Topic: Synthesis of p-dialkoxylbenzene from p-benzoquinone  (Read 2115 times)

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Offline GammaGoblin

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Synthesis of p-dialkoxylbenzene from p-benzoquinone
« on: October 21, 2008, 07:02:10 PM »
I'm struggling to figure out the mechanism for the following reaction.

                        KOH/EtOH
p-benzoquinone ------------> p-dialoxybenzoquinone
                            R-Br
where R-Br is a primary haloalkane.

I suspect that this has something to do with the R-Br + OH- -> R-OH + Br- but I'm not sure where to go from there. I have a feeling like the bromide ion is involved but am not sure how. I tried working backwards from the p-dialkoxybenzoquinone to a likely precursor, hydroquinone, but I'm not sure where to go from there.

Many thanks.

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