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i'll just leave this here

- Mon, 27 Mar 2017 03:58:41 EST 6p22FvVe No.78612
File: 1490601521191.png -(43318B / 42.30KB, 414x524) Thumbnail displayed, click image for full size. i'll just leave this here
cf piperine, phenylacetic acid, etc.
press - Wed, 05 Apr 2017 06:42:04 EST Jirf0CGs No.78622 Reply
i dont think youll have a lot of fun doing an ozonolysis on a multigram scale.
Jack Pattingspear - Fri, 07 Apr 2017 19:09:55 EST Rb652zpr No.78628 Reply
'Swhy I put "or" the tungstic acid route. Ozone is there for anyone who wants to use it. Only downside of H2WO4 is that the paper uses t-butanol/water as solvent. In this case you might get away with acetone or GAA as the cosolvent. AFAICT the cosolvent is just there to solubilize the alkene so replacing t-butanol should be easy.

Ref is Chem Lett 18 (5) 1989 pp 857-60. The first reaction is the dithionite reduction of dienoic carboxylic acids, Chem Lett 1982 by Camps et al.
press - Sun, 09 Apr 2017 18:52:45 EST NC1/aXOS No.78630 Reply
oh damn, i completely overlooked that, sorry. guess my attention span in affected by some

im not familiar with how common tungstic acid is or how easy tungstic acid is to produce but i can see the appeal, a lot more elegant than trying demethylations on vanilin. i guess if you melt sodium and throw in tungsten at a reasonable mesh youd get something you could turn into tungstic acid, i dunno im a fucking noob at gen chem.
Sophie Sivingbanks - Tue, 11 Apr 2017 18:04:06 EST IJDWDsu9 No.78632 Reply
It looks like heating the tungsten in bleach containing a little mercuric nitrate works:


Tungsten trioxide is soluble in alkali but not acid which gives some idea of how to separate it from other metals if an alloy such as tungsten steel is digested. In this patent H2O2 is used to selectively dissolve tungsten over aluminium:


However alloys may not dissolve in H2O2 because of passivation. If pure tungsten is available it may even be possible to dissolve this in the rxn mixture directly forming tungstic acid in situ.
Rebecca Clapperbare - Mon, 17 Apr 2017 19:51:12 EST 6Uohuwu9 No.78640 Reply
Tungsten costs a few tens of dollars per pound. I was excited to use tungsten instead of ruthenium which is about $50/ounce or indium which is similar. Additionally tungsten is widely used in tools which are OTC whereas runthenium and indium are only used in electronics. About one ounce of tungstic acid is used to cleave 100 grams of piperic acid.

Sesamol is impractical. The content of sesamol in sesame oil is less than 1%. I spent years developing routes from sesamol and felt like an idiot when I realized this.
Charlotte Hurringchare - Tue, 25 Apr 2017 18:52:15 EST UoTssc8h No.78643 Reply
What about forming the diol with peroxide and base then cleavage with nickel?

This paper shows 1,2-cyclohexanediol can be cleaved to adipic acid just by dumping it in with some bleach and nickel nitrate/acetate: http://pubs.acs.org/doi/abs/10.1021/jo0612574. Theoretically this should yield the aldehyde if the nickel oxidant were instead isolated and the reaction done under anhydrous conditions.
Martin Dicklecocke - Sun, 14 May 2017 10:17:15 EST UoTssc8h No.78651 Reply
Has anyone tried the dithionite reduction of piperinic acid? The source OP cited only has info on reducing acids with aliphatic side chains and I'm thinking that conjugation with the aromatic ring might cause the beta-gamma unsaturated acid to re-arrange to the gamma-delta or otherwise muck something up

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