From: nobody@nowhere.com   
      
   On 2015-07-03 11:19 PM, durabol74@gmail.com wrote:   
   > On Friday, July 3, 2015 at 4:13:46 AM UTC-6, yyy378 wrote:   
      
   > Thanks for the response. I now think I can use a dropping funnel.   
   > I've come up with this tentative procedure that I will post here   
   > for review: 2g sodium borohydride in 100ml methanol is added drop wise   
   > over 20m to 5g of the ketone in 100ml methanol, let sit 70m or add   
   > acid(acetic or HCl) until slightly acidic, evaporate or add 500ml   
   > ice water to precipitate the diol.   
   > Brock   
   >   
      
   When neutralized NaBH4 yields boric acid or its salt. I seem to recall   
   that boric acid reacts with a diol to yield a cyclic compound or worse a   
   polymer. E.g. see:   
      
   Crosslinking Mechanism of Boric Acid with Diols Revisited   
      
   Marcel Rietjens1,2 and   
   Peter A. Steenbergen1,3   
   European Journal of Inorganic Chemistry   
   Volume 2005, Issue 6,  pages 1162–1174, March 2005   
      
      
   In my opinion your work up is based upon too much hope and not enough   
   skepticism. I think a more conventional work up would entail transfer of   
   product between aqueous phase and an immiscible organic phase. Don't you   
   think it would be wise to consult an organic lab manual or prior   
   literature in addition to this usenet group?   
      
   --- SoupGate-Win32 v1.05   
    * Origin: you cannot sedate... all the things you hate (1:229/2)