Natural Science Forum / Chemistry / Organic Synthesis / March 2005

As a fellow student I know that certain 'exact recipies' aren't always
easy to find. The way I would go about breaking this down would be to
first protonate the glycerol to form at least one alkene in the
molecule, then cleave the molecule with O3 in dimethyl sulfide
(ozonolosys). This should yield two different molecules, formadlehyde
and a two carbon enol thinger. To the formaldehyde use NaBH4 or rainey
(Ni2-H) to reduce it to methanol. Then to the enol add NaBH4 to make it
into 1,2-ethyl-diol. Then protonate to form ethyne. From there use a
little rainey nickel to saturate to an alkene then add some regular old
d.i. water to hydrate the double bond into ethanol. This methodology is
quite expensive nor have I done it experiementally so take what I have
suggested with a grain of salt. I will say however, that all reactions
and steps are correct a la 'Org. Chem.' 5th ed. by Wade. What I don't
know is any certain solvents (aside from dimethyl sulfide) or reaction
temperatures or whether or not these things are available to you. Good
luck.