Piperonyl Alcohol To Piperonal?

Blammo

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Is the method, posted here, of reacting benzyl alcohol with HBr in DMSO applicable to piperonyl alcohol, producing piperonal?
 

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Blammo

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Why not?
 

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I may not have been clear. Does substituting piperonyl alcohol for benzyl alcohol produce piperonal, liek how using benzyl alcohol produces benzaldehyde
 

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I dont know the method you are refering to but I am sure that piperonyl alcohol + HBr will lead to a very different reaction than benzyl alcohol due to the
 

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I dont know the method you are refering to but I am sure that piperonyl alcohol + HBr will lead to a very different reaction than benzyl alcohol due to the
 

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I dont know the method you are refering to but I am sure that piperonyl alcohol + HBr will lead to a very different reaction than benzyl alcohol due to the
 

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... Methylenedioxy group attached to the benzene ring. I guess HBr would be capable of cleaving the ether and would probably do so before replacing the Hydroxy group. A Controlled oxidation reaction of alcohol to aldehyde is certainly possible though
 

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There is a video on this forum of benzyl alcohol being oxidized to the aldehyde in dmso, with hbr or bromine, i think.

I see your point though, maybe too acidic.

What do you think about dilute nitric acid and catalytic amounts of sodium nitrite to do this process?
 

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As I said I am not familiar with the Benzyl Alcohol + HBr reaction but it does not seem like the general idea is an oxidation of the alcohol to the corresponding aldehyde.

I think that HBr would lead to a substitution of the OH-group to Br which would give you benzyl bromide - a very useful reagent far far more interesting than Benzaldehyde. Benzaldehyde can be easily obtained and the oxidation of benzyl alcohol to benzaldehyde can be done in numerous ways with pretty high yield and easy workup, there is no need for HBr to do this and also not a feasible way.

Piperonyl Alcohol is about as easy to obtain as Piperonal itself - both not too hard to get actually so I guess you are mixing a few things up. The BA + HBr reaction is certainly a viable route to amph precursors but it will not work on Piperonyl Alcohol because the ether will be cleaved first, that is one typical use of HBr actually, cleavage of a methoxy group from a benzene ring so not going to work anyway but I highly doubt that your desired product is piperonal ... which is as I said not that hard to get but also quite a way to go from there to MDA or MDMA. Yes it can be done and Piperonyl Alcohol can most likely be easly oxidized with high selectivity to piperonal without over-oxidation to the carboxylic acid but no nitric acid and sodium nitrite are at least not common reagents for this and I doubt that anything useful would be produced by that.
 
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