dormouse (Member)
04-21-00 07:17
No 108485
      A substitute for benzoquinone? -spiceboy  Bookmark   

Author  Topic:   A substitute for benzoquinone? 
spiceboy
Member   posted 08-27-98 11:12 AM          
--------------------------------------------------------------------------------
Is it possible that;
You could oxidize napthalene into napthaquinone and use this as a substitute for benzoquinone in a catalytic oxidation?
The reason I ask this is that the molecule appears to be identical to benzoquinone except that it has 2 rings. The oxygen appears to be in the right places...
It sure would be easy to make,at least to my thinking, from moth balls(99.8% napthalene)
and dichromate...maybe even KMnO4......??????
 
Bright Star
Member   posted 08-27-98 03:34 PM          
--------------------------------------------------------------------------------
Thats a very interesting thought. I bet it would work..... Geometry is the same ....
Don't suppose ya got a ref?
 
spiceboy
Member   posted 08-28-98 09:25 AM          
--------------------------------------------------------------------------------
No, I dont have a ref, as I have never even heard of such craziness.
I found the spark for the idea in an ancient
1958 organic textbook someone threw away at my local University. The author was talking about oxidation of ringed systems, and the structure of Napthaquinone caught my eye.
Hell, I dont see why you couldn't do it either. You can bet someone will have more soon.....mothballs are cheap.
 
Rhodium
Administrator   posted 08-28-98 06:18 PM          
--------------------------------------------------------------------------------
Vogel, Ed III, condensed synth:
120g CrO3 in 150ml 80% HOAc in a 2000ml 3-neck flask, w/ thermometer, stirrer and 1000ml dropping funnel. Cool flask in ice/salt mixture. When the temp has fallen to 0C, add a solution of 64g naphtalene in 600ml HOAc during 2-3h, maintaining an internal temp of 10-15C. Stir overnight, and let solution attain room temp. Allow dark green soln to stand for 3 days, stir occasionally. Pour rxn mixture into 5000ml H2O, and collect naphtoquinone by suction filtration, wash with 200ml H2O and dry in a desiccator. Recrystallize from 500ml pet ether. Yield 17g, mp 124-125C.


Piglet
Member   posted 08-31-98 07:06 AM          
--------------------------------------------------------------------------------
Why are you looking for a substitute? Isn't benzoquinone pretty easy to get OTC? Or is there a practical advantage you have spotted?
Also, will benzoquinone work as an oxident in the CH3OH version of #3? I have no idea on this subject.
Piglet