Allyl alcohol is produced commercially by the
Olin and
Shell corporations through the hydrolysis of
allyl chloride: : Allyl alcohol can also be made by the rearrangement of
propylene oxide, a reaction that is catalyzed by
potassium alum at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of
propylene to
allyl acetate: : Hydrolysis of this acetate gives allyl alcohol. In alternative fashion,
propylene can be oxidized to
acrolein, which upon
hydrogenation gives the alcohol. In principle, allyl alcohol can be obtained by
dehydrogenation of
propanol.
Laboratory methods In the laboratory,
glycerol reacts with
oxalic or
formic acids to give (respectively)
dioxalin or glyceric formate, either of which
decarboxylate and
dehydrate to allylol. Allyl alcohols in general are prepared by
allylic oxidation of
allyl compounds, using
selenium dioxide or
organic peroxides. Other methods include carbon-carbon bond-forming reactions such as the
Prins reaction, the
Morita-Baylis-Hillman reaction, or a variant of the
Ramberg-Bäcklund reaction. Hydrogenation of
enones is another route. Some of these methods are achieved by the
Luche reduction,
Wharton reaction, and the
Mislow-Evans rearrangement. Allyl alcohol was first prepared in 1856 by
Auguste Cahours and
August Hofmann by
hydrolysis of
allyl iodide. ==Applications==