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Benzaldehyde + Ac2O
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Topic: Benzaldehyde + Ac2O (Read 11970 times)
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Benzaldehyde + Ac2O
«
on:
September 07, 2004, 08:52:43 PM »
Benzaldehyde + acetyl anhydride in the presence of NaOAc. What kind of reaction is this? Just a common carbonyl alpha-substitution or something else? What do we get?
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Organic Minion
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Re:Benzaldehyde + Ac2O
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Reply #1 on:
September 08, 2004, 12:49:28 AM »
It's not an alpha substitution, there are no alpha protons in benzaldehyde. I think that those are acylation conditions. Sort of like Friedel-Crafts, but without a metal Lewis acid. I think that you would get 3-formyl acetophenone.
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falcon
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Re:Benzaldehyde + Ac2O
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Reply #2 on:
September 08, 2004, 05:07:22 AM »
It`s classic Perkin condensation! Synthesis of cinnamic (3-phenyl-2-propenoic) acids. Acetate anion
tears off the proton from acetic anhydride, this anion attack carbonyl group in benzaldehyde, further follows migration negative charge, leading to cinnamic acid.
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Re:Benzaldehyde + Ac2O
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Reply #3 on:
September 08, 2004, 06:28:06 AM »
That's right... thanks, I see now.
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Re:Benzaldehyde + Ac2O
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Reply #4 on:
September 08, 2004, 12:04:05 PM »
Really? But the acetate anion isn't nearly a strong enough base to remove that proton!
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Re:Benzaldehyde + Ac2O
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Reply #5 on:
September 08, 2004, 01:11:08 PM »
I stand corrected. Falcon was right on. Here is a link with some references if anyone is interested:
http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/ONR300.htm
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Benzaldehyde + Ac2O