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Topic: Diacetal directly to aldehyde by... magic?  (Read 2502 times)

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Offline wonka_vision

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Diacetal directly to aldehyde by... magic?
« on: September 19, 2010, 07:28:00 PM »
Hi everyone,

I've been following a published synthesis that is supposed to allow me to produce an aldehyde-functionalized methacrylate monomer.

The initial synthesis step was to react methacroyl chloride with aminoacetaldehyde dimethylacetal to form the diacetal monomer.
The paper I was following then stated a deprotection step was done by reacting the monomer in ~20 % acetic acid at 100 C for 3 hours. Finally, the resulting 1,2-diol was reacted with sodium periodate to generate an aldehyde.

However, when I performed the second step, the diacetal was converted directly to an aldehyde. I can't explain how this happened without any obvious oxidizer present, and I know my PhD committee is going to ask me about it.

Does anyone have any idea how this could happen?

Thanks!

 

Offline MissPhosgene

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Re: Diacetal directly to aldehyde by... magic?
« Reply #1 on: September 19, 2010, 08:38:14 PM »
Hi,
  Write the mechanism for acetal hydrolysis and you will know!

Best.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline wonka_vision

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Re: Diacetal directly to aldehyde by... magic?
« Reply #2 on: September 19, 2010, 11:28:47 PM »
Well there you go.   ::)

Thanks!


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