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Topic: DIRECT CONVERSION OF EPOXIDE TO DIACETALS  (Read 2987 times)

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Offline RAMKI

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DIRECT CONVERSION OF EPOXIDE TO DIACETALS
« on: April 25, 2008, 07:33:23 AM »
Am involved in isomerisation of styrene oxide to phenyl acetaldehyde.To make the dimethyl acetal, phenyl acetaldehyde is either reacted with the TMOF,trimethyl orthoformate or for economic reasons with methanolic HCL.Is there a direct way of reacting stryene oxide in a one-pot reaction to the dimethyl acetal?
Normal reactions with SO and ALCOHOLS produce a mono acetals.
Have tried most of the available catalysts including Bismuth Triflate.
If somebody has had success in similar reactions,do share the information.
 

Offline sjb

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Re: DIRECT CONVERSION OF EPOXIDE TO DIACETALS
« Reply #1 on: April 28, 2008, 11:42:51 AM »
What kind of Lewis acids catalyse the epoxide -> aldehyde rearrangement? I've only really seen this as a footnote in Clayden, so don't kow typical conditions.

Does the order in which you add the reactants make a difference - could it be that the epoxide reacts preferentially to the aldehyde with the alcohol?

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