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Author: Subject: Piperonyl Butoxide to Safrole?
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[*] posted on 3-4-2014 at 17:15
Piperonyl Butoxide to Safrole?


Is there a way to cleave the ether on the alpha carbon without damaging the methylenedioxy ring? And how about the double bond on the propyl side chain to form Safrole?


200px-Piperonyl_butoxide.png - 13kB200px-Safrole-Line-Structure.png - 6kB
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[*] posted on 3-4-2014 at 17:59


Might be possible to strongly oxidize those alkyl chains to dibenzoic acid, decarboxylate both, halogenate, resolve products, Friedel Crafts alkylate, then re-etherify the cleaved bridge from the vicinal diphenol. Why do you ask?
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[*] posted on 3-4-2014 at 18:41
Retrosynthesis


Piperonyl butoxide is made by etherification and chloromethylation starting from dihydrosafrole which is derived from safrole :) Hoping to cleave one ether without cleaving another is what is known as wishful thinking :D The question posed should be are any of these reactions reversible with a change of equilibrium :P That's the answer and the end really does result from the effort applied :cool:



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[*] posted on 7-4-2014 at 17:41


No way Jose.
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