Author Topic: Error in MM's Wacker (benzo) oxidation write up???  (Read 6020 times)

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  • Guest
Error in MM's Wacker (benzo) oxidation write up???
« on: November 29, 2003, 06:21:00 AM »
I was comparing Methyl Man and Brightstars write ups for the p-benzo wacker and I'm probably wrong but I may have found an inconsistency. Both procedures use relatively the same amount of safrole, PdCl2, and p-benzo, and the only real difference is the reaction medium; 400ml methanol in MM's write up and 300ml DMF in the Brightstar write up. Anyway, after the wacker reaction is complete, MM indicates to create 1.7L 3N (~10%) HCl solution using 500ml of 31% HCL and flood the reaction mixture with it. Brightstar, on the other hand, indicates to create the HCL solution with only 50ml of HCl (Muriatic Acid, same as 31% HCL) and 1.5L of water. Why is there such a big difference between the amount of HCl used to create the HCl/dH2O solution for flooding the reaction contents?


  • Guest
it doesn't really matter exactly how much HCl...
« Reply #1 on: November 29, 2003, 07:14:00 PM »
it doesn't really matter exactly how much HCl is used as it isn't a reagent that is consumed, what you want is something between 5-10% HCl

the solution is made acidic so you will get a better seperation of ketone, if it were basic you would get emulsions and headaches

there was also some speculation with O2 wackers that HCl was necessary to hydrolyse the post wacker product to ketone, but as far as Ab2 is concerned O2 wackers were good for one thing - marketing PdCl2


  • Guest
p-benzo ammount
« Reply #2 on: November 29, 2003, 08:36:00 PM »
I think BS uses less p-benzo than MM. Also, I have seen some old Wacker recipes, slightly different than BS but pretty much the same thing, that uses the same molar quantity of safrole and p-benzo ( very small excess of p-benzo ).


  • Guest
inhibitory chlorides
« Reply #3 on: February 24, 2004, 04:50:00 AM »
it seems that chlorides inhibit the reaction progress. does no-one use a molar equivalent ammt of Pd(OAc)2?


  • Guest
using equimolar amounts of benzo and some...
« Reply #4 on: February 26, 2004, 12:56:00 AM »
using equimolar amounts of benzo and some extra pdcl2, swim gets 140-150g ketone each wacker.  using 150g benzo as in the mm writeup is wastefull.