If you use xylene, you could do a simple reflux with your acid, alcohol and sulfuric acid and still push the reaction to completion. With xylene, I
have seen a water layer forming at the bottom.
So the water separates in the reaction vessel. I was running a Dean Stark with xylene for the first time some time ago and couldn't collect any water
in the trap, but even while boiling I got two layers and after work-up a near quantitative yield (diketal of a ketone with ethylene glycol).
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