Jan1983 (Hive Bee)
06-17-02 11:33
No 322393
      piperonylic acid  Bookmark   

Hi guys, again piperine piperidine piperic acid and so on,

here a question:

Can "piperonylic acid or the alcohol" also be used as a source for piperonal ?

Greets
 
 
 
 
    OB1KNoBee
(Stranger)
06-18-02 01:39
No 322557
      no  Bookmark   

Don't think so... stick to the sure thing.

GOOD GOOD
 
 
 
 
    PrimoPyro
(Hive Prodigy)
06-18-02 04:56
No 322619
      The alcohol can be oxidized to the aldehyde ...  Bookmark   

The alcohol can be oxidized to the aldehyde (which is piperonal) and technically LAH could reduce the acid (an ester of it) to the alcohol, ready for oxidation. But the practicality of this is very small.

The piperonyl alcohol would be a good source if it was cheap for you to get. smile

                                                    PrimoPyro
 
 
 
 
    Jan1983
(Hive Bee)
06-18-02 07:33
No 322639
      The alcohol: 100 g = 45 cheap enough ?  Bookmark   

The alcohol:

100 g   =  45

cheap enough ?

what can be used to oxidise the stuff ?? KMnO4 ? H2O2 ?

anyone has ref's ?
 
 
 
 
    Antoncho
(Official Hive Translator)
06-18-02 11:35
No 322673
      UTFSE!  Bookmark   

Fe(NO3)3




Antoncho
 
 
 
 
    PrimoPyro
(Hive Prodigy)
06-18-02 14:25
No 322704
      Haha  Bookmark   

We so very rarely here that tone from you, Antoncho. laugh

As Antoncho says, ferric nitrate is the known method here. I bet cupric acetate with ammonium nitrate oxidation would work as well without overoxidation. It is a very gentle reducing agent.

KMnO4 will very likely yield the carboxylic acid. I don't know how H2O2 would fare at all, personally. I myself would stick with ferric nitrate since it has been documented here.

Reduction of the acid ester with LAH to the alcohol, then oxidation to the aldehyde, is not worth all the effort just for some piperonal. LAH is damn expensive, and should be saved for more important steps, i.e.reduction of nitrostyrenes etc.

                                                 PrimoPyro
 
 
 
 
    Antoncho
(Official Hive Translator)
06-18-02 18:28
No 322739
      Another way  Bookmark   

I forgot to mention that for those who, unlike swim, aren't financially challengedsmile, PtO2 and oxygen is the best possible way. A very general and selective/high-yielding oxidation.


Antoncho

P.S. Primo: wink
 
 
 
 
    terbium
(Old P2P Cook)
06-18-02 19:11
No 322751
      Cupric/ammonium nitrate  Bookmark   

I bet cupric acetate with ammonium nitrate oxidation would work as well without overoxidation. It is a very gentle reducing agent.
Any reputable references to this procedure? I was under the impression that it was just someones pipe dream.
 
 
 
 
    Rhodium
(Chief Bee)
06-18-02 19:42
No 322756
      The references I have seen on that oxidizing ...  Bookmark   

The references I have seen on that oxidizing system deals with the oxidation of hydroxyketones to 1,2-diketones - I don't know its scope outside this.
 
 
 
 
    PrimoPyro
(Hive Prodigy)
06-18-02 20:51
No 322764
      Arg  Bookmark   

My references for that would be in TFSE, in posts that represent it as fact rather than novelty. I hate when TFSE is wrong or incomplete. frown

                                                PrimoPyro