Stramonium - 19-7-2007 at 22:37
I'm looking at ways of converting benzoin to desoxybenzoin. Unfortunately HI reductions are out.
Would a suitable strategy be to reduce benzoin with NaBH4 to the diol and then rearrange to a ketone with 15% aqueous H2SO4 (as made popular in many
diol/epoxide to ketone rearrangements in the clandestine synthesis of phenyl-2-propanones)?
I would prefer to avoid Zn/Hg reduction of the ketone, followed by oxidation of the alcohol.
Another strategy mentioned on Orgsyn (http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2...) is the reduction of benzil (ref. Japp and Klingemann, J. Chem. Soc. 63, 770
(1893) ) but I cannot access this article through ACS Publications online. I have no problem using benzil as an intermediate so if anyone has access
to this article and could outline the experimental section that would be great.
If anyone has any input I would greatly appreciate it.
Thanks in advance.
Reference Information
solo - 20-7-2007 at 00:41
Reduction of a-Diketones
FRANCIS R. JAPP, F.R.S., and FELIX KLINGEMAKN, Ph.D.
J. Chem. Soc. 63, 770 (1893)
Attachment: Reduction of a-Diketones.pdf (364kB)
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