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Topic: Why such low yield of diphenylacetylene?  (Read 1856 times)

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Offline tdod

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Why such low yield of diphenylacetylene?
« on: November 23, 2013, 01:41:02 PM »


My yield was low (28%) and I am wondering if there is some feature of the chemistry that makes this low yield. The only work up was vacuum filtration and an ethanol wash, so unless a side-product was produced then i can't figure out what happened to the yield. Reaction progress wasn't monitored bny TLC but it was heated at 160˚C for ten minutes.

Thanks!
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Offline discodermolide

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Re: Why such low yield of diphenylacetylene?
« Reply #1 on: November 23, 2013, 02:29:46 PM »
If your yield was only 28% what is the rest of the material?
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Offline spirochete

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Re: Why such low yield of diphenylacetylene?
« Reply #2 on: November 23, 2013, 05:21:34 PM »
Maybe the high temperatures cause decomposition of the starting material? Maybe try a lower temperature and a stronger base?

Or you're getting significant amounts of substitution product for some reason? Lilke disco said you need to give us more info.
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Offline zsinger

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Re: Why such low yield of diphenylacetylene?
« Reply #3 on: November 23, 2013, 07:01:06 PM »
The second elimination would probably need a stronger base, or higher temperatures.  But, as Spiro said, we need all rxn. conditions to better help you :).
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