MD Bezyl Alcohol To MDP-2-P

[Rasputin]

I was wondering if MD BenzylAlcohol would be a viable route to MDP-2-P. I read on Rhodiums site that Benzyl alcohols could be turned into their corresponding Aldehydes via the Jones Reagent. If this is the case could I take the methylene dioxy benzaldehyde and perform the Aldol condensation described in Two Dogs P2P procedure, then performing the Bayer-Villager oxidation on the unsaturated ketone resulting in MDP2P? Search engine is down so I'm left to ask. Any comments welcome thanks in advance
                     ~a safrol deprived chemist

[xxxxx]

i have a document from the chemical society of japan (1957) that might be relevant. how do i post a scan (2 pages), or do i type the article (there are some diagrams which would be omitted).

[Kinetic]

It all depends what reagents you have at your disposal.

I'd be surprised if a standard

Jones Oxidation

(http://themerckindex.chemfinder.com/TheMerckIndex/NameReactions/ONR207.htm) didn't give you a lot of piperonylic acid rather than piperonal. This is the case according to the Merck Index link. There is a nice

Swern

(http://themerckindex.chemfinder.com/TheMerckIndex/NameReactions/ONR390.htm) type oxidation on Rhodium's page:

DMSO Oxidation of Benzyl Alcohols to Benzaldehydes

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzaldehydes.dmso.html) which gives great yields and uses readily available reagents. There may be a possiblity of ether cleavage with HBr in polar aprotic solvents at 100^oC but this is by no means a certainty. Methoxies certainly survive intact.

From there I'd suggest Barium's excellent thread (read the entire thread)

Post 333551

(Barium: "benzaldehydes to phenylacetones", Novel Discourse).

Two simple steps and both great yielding. The most difficult reagent to aquire (by a long way) should be piperonyl alcohol. Once you've got that it should be plain sailing from there.


Edit: 'how do i post a scan (2 pages)' can be answered in the FAQ. Simply scan your article, save it, and upload the file from your computer. Then link the article to your post using the upload feature.

[Rasputin]

Thank you very much you answered my questions perfectly and gave bee many ideas

once again thanks