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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: wonka_vision on September 19, 2010, 07:28:00 PM

Title: Diacetal directly to aldehyde by... magic?
Post by: wonka_vision 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!

 

Title: Re: Diacetal directly to aldehyde by... magic?
Post by: MissPhosgene on September 19, 2010, 08:38:14 PM

Hi,
  Write the mechanism for acetal hydrolysis and you will know!

Best.

Title: Re: Diacetal directly to aldehyde by... magic?
Post by: wonka_vision on September 19, 2010, 11:28:47 PM

Well there you go.   ::)

Thanks!