Sciencemadness Discussion Board

Protocatecualdehyde > Piperonal ?

NewTopic - 1-4-2019 at 00:34

I've read through a few forums and articles regarding this methylenation but i'm just trying to get the most accurate information when completing this.

For Instance;
https://erowid.org/archive/rhodium/chemistry/methylenation.h...

Is there anyway around using the autoclave other then using dibromomethane to replace in the process or is there any other method that would work as an alternative.

This seems the easiest, most of the chemicals are quite easy to obtain and reasonably priced for my country / within laws except the end product.

Any advice ?

Loptr - 1-4-2019 at 04:21

UTFSE to find the existing threads on this subject.

Chemi Pharma - 1-4-2019 at 15:59

May be this article will be interesting for you.:)

Also @Bipolar posted an interesting work up about the methylenation of 5-hydroxy vanillin to Myristicinaldehyde using DCM here: http://www.sciencemadness.org/talk/viewthread.php?tid=147026...

Attachment: protocatechualdehyde, vanillin and piperonal with glyoxylic acid from cathecol and benzodioxole.pdf (178kB)
This file has been downloaded 555 times

[Edited on 2-4-2019 by Chemi Pharma]

morganbw - 2-4-2019 at 14:47

Quote: Originally posted by Chemi Pharma  
May be this article will be interesting for you.:)

Also @Bipolar posted an interesting work up about the methylenation of 5-hydroxy vanillin to Myristicinaldehyde using DCM here: http://www.sciencemadness.org/talk/viewthread.php?tid=147026...



[Edited on 2-4-2019 by Chemi Pharma]


That last paper is sweet, I am pretty sure that I have multiple copies of it.
Still rocks.

bipolar - 3-4-2019 at 02:01

Quote: Originally posted by NewTopic  
Any advice ?

Use conditions similar to described here - http://www.sciencemadness.org/talk/viewthread.php?tid=147026...
And for work-up - just dilute reaction mixture with water and do a steam distillation, as piperonal is very volatile with steam.


and learn how to UTFSE

CycloKnight - 3-4-2019 at 13:15

Protocatechualdehyde methylenation isn't difficult to do with dichloromethane in DMSO.
See the attached pdf of the method I posted here 5 yrs back.

Attachment: Prototocatechualdehyde Methylenation.pdf (560kB)
This file has been downloaded 682 times