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Question

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In this reaction I am able to figure all reaction except first. What confuses me is the fact than in solution, the cyclic diol reacts only with the aldehydic group. But It can also react with the ketone right?

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  • $\begingroup$ This is another poorly worded question in that the conditions for A to B require more detail to be certain of the identity of B. From the rest of the question I surmise that B is 2-(1,3-Dioxolan-2-yl)cyclohexanone i.e. the keto-aldehyde with dioxane protection on the aldehyde. Incidently I can find no reference to this compound by googling its name. Can someone with database access cast any further light on this? $\endgroup$
    – Waylander
    Apr 27, 2020 at 9:18
  • $\begingroup$ @Waylander: For the ketoaldehyde (hydroxymethylene cyclohexanone), the dioxolane does not appear to have been formed in the usual way. I didn't look at all 214 pages in Chem Abst. But it has been made from the TMS enol ether of cyclohexanone, 2-methoxy-1,3-dioxolane and Lewis acid. The traditional ketalization with, H+, ethylene glycol and the hydroxymethylene (CHO) derivative of alpha-tetralone appears to be doable. $\endgroup$
    – user55119
    Apr 27, 2020 at 16:11
  • $\begingroup$ Interesting! Thank you for that. The enol mix of the alpha tetralone CHO analogue may be different to cyclohexyl equivalent which may influence the viability of this reaction. $\endgroup$
    – Waylander
    Apr 27, 2020 at 16:16

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