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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Woodwardt84 on November 27, 2011, 04:59:57 AM

Title: Work up of carboxylic acid acetal
Post by: Woodwardt84 on November 27, 2011, 04:59:57 AM

Im a little bit confused on how to make a work up to the reaction in the pic.
I want to protonate the acid but to do that i guess i have to get down to pH 3-4 but I'm worried that the acetal breaks down at pH that low. Any clever work up suggestion?
Further i want to transform the carboxylic acid to acyl chloride with SOCl2

Title: Re: Work up of carboxylic acid acetal
Post by: orgopete on November 27, 2011, 07:19:56 AM

I think you can safely do this. The carbonyl groups will reduce the basicity or stability of any intermediate carbocation that must form in a hydrolysis reaction. So the reaction would be very slow. (You can further decrease the rate by keeping it cold. My favorite work up strategy is to add ice to my reactions to keep them cold.)

The second point is that the sequence proposed appears to be a known literature sequence. I think it is highly probable that you could simply go to your library, look up the two compounds in SciFinder, and find published methods for their preparation.