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Author: Subject: Synthesis of 3-(p-Hydroxyphenyl)-2-Butanone "raspberry ketone"
International Hazard

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[*] posted on 30-6-2016 at 05:21

on the 2nd page of this thread,klute tried to reduce the enone using Zn/AcOH, but failed since he could not separate the products-
The slightly pink aqueous mixture was extarcted with AcOEt and the solvent evaporated afetr been washed with brine, togive a viscous, raspberry-smelling paste. Attempts to cristallize this with various solvents and conditiosn were all fruitless.
I thought about this and remembered a method someone had told a long time back in one of my posts.That method used Zn/HCOOH and had an easy way to remove the Zn- formate formed.
could this method give a cleaner product ?
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Dennis A

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[*] posted on 2-6-2018 at 01:08

Many years ago i tried the acid catalyzed Adol on 4-Methyl-Benzaldehyde with MEK/Butanone hoping to obtain 4-Methyl-BMK intermediate having extremely limited equipment on hand and being very inexperienced at the time was no doubt the reasons for my failures however in light of this i just could never manage to find out where the problem arose from

Reagents were always of high purity the reaction after full addition was left with strong stirring for periods between 18-24 hours as i had work among other things the red-ish reaction mixture was observed every time

Using 37% HCL acid in place of HCL gas as generating gases in that location was a definite no no and would have led to almost certain demise of ones self did others others encounter problems when using acid instead of gas ? Maybes it was the particular substrate although i find it very unlikely i seam to fine more base catalyzed Adols than acid catalyzed on Anisaldehyde/4-MeO-Benzaldehyde for example

I am old and rusty please forgive am i wrong to assume that the base catalyzed adol reaction of Benzaldehyde with Mek/Butanone would produce a intermediate that could be subjected to a reaction that i,m forgetful to name to produce propiophenone ?

EDIT - Thanks in advance just trying to clear up some loose ends maybe i,l give it another shot soon its one of the few reactions i never got to work i never forgot about it the feeling of being defeated haunts me



[Edited on 2-6-2018 by Dennis A]

[Edited on 2-6-2018 by Dennis A]
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