Sciencemadness Discussion Board

Piperonyl Butoxide to Safrole?

Hey There - 3-4-2014 at 17:15

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

Chemosynthesis - 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?

Retrosynthesis

leu - 3-4-2014 at 18:41

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:

zed - 7-4-2014 at 17:41

No way Jose.