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Topic: Organic synthesis problem  (Read 2054 times)

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Offline justinschramm05

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Organic synthesis problem
« on: March 18, 2014, 09:58:15 PM »
I have an organic synthesis problem that's been bugging me for awhile.  Starting with Oxalic acid, I need to make 3-oxobutanal.  I just don't know where to start.  It won't de-carboxylate when heated right?
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Offline AlphaScent

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Re: Organic synthesis problem
« Reply #1 on: March 19, 2014, 11:28:47 AM »
From Oxalic acid, that is a good question??

What about a crossed aldol condensation between acetone and formaldehyde?? 

The aldehyde is much more reactive towards the enol than acetone.

Then do PCC or swern of the alcohol to yield your product.
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Offline pazgomenskii

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Re: Organic synthesis problem
« Reply #2 on: September 02, 2014, 10:57:48 AM »
Please, AlphaScent, can you give conditions that will favor the above Acetone & formaldehyde aldol condensation or you think the same condition that favor Acetone to Acetone self Aldol condensation will favor this Acetone/ Aldehyde heterogeneous condensation? Thanks in advance for anticipated cooperation.
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Offline orgopete

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Re: Organic synthesis problem
« Reply #3 on: September 02, 2014, 10:49:27 PM »
Acylate ethyl vinyl ether and hydrolyze?
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