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Author: Subject: Dihydrocodeine O-demethylation?
jon
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[*] posted on 31-12-2006 at 23:33


yes, there was a discussion on this at synthetikal.org just before they went offline it gave a reference for this being done in hydrobromic acid dissolved in acetic acid the HBr was 10%.
I had a reference in Chem. Ber. but it was too old the library did'nt have it.
hydrocodone is demethylated by 48% (aq) hydrobromic acid in 95% yeilds. I guess they use 10% HBr in this case is the 6-OH group likes to react SN2, maybe I'm wrong.
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Biginelli
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[*] posted on 1-1-2007 at 04:36


SN2 in such polar conditions?
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jon
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[*] posted on 2-1-2007 at 10:56


maybe dehydration which is an E-1 or E-2 reaction followed by (markovnikov) addition, i dunno i just know that's the conditions i read on specifically dihydrocodiene. yet for hydrocodone the acid used is aqueous HBr. so the 6 keto, and the 6- hydroxy react differently to acids.
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