Editing 1-Hexanol (section)

==Preparation==
Hexanol is produced industrially by the oligomerization of [[ethylene]] using [[triethylaluminium]] followed by oxidation of the [[organoaluminium|alkylaluminium products]].<ref name="Ullmann">{{Ullmann | first1 = Jürgen | last1 = Falbe | first2 = Helmut | last2 = Bahrmann | first3 = Wolfgang | last3 = Lipps | first4 = Dieter | last4 = Mayer | title = Alcohols, Aliphatic | doi =  10.1002/14356007.a01_279}}.</ref>  An idealized synthesis is shown:
:Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> + 6C<sub>2</sub>H<sub>4</sub> → Al(C<sub>6</sub>H<sub>13</sub>)<sub>3</sub>
:Al(C<sub>6</sub>H<sub>13</sub>)<sub>3</sub> + {{frac|1|1|2}}O<sub>2</sub> + 3H<sub>2</sub>O → 3HOC<sub>6</sub>H<sub>13</sub> + Al(OH)<sub>3</sub>
The process generates a range of oligomers that are separated by [[distillation]].

===Alternative methods===
Another method of preparation entails [[hydroformylation]] of [[1-pentene]] followed by [[hydrogenation]] of the resulting aldehydes.  This method is practiced in industry to produce mixtures of isomeric C<sub>6</sub>-alcohols, which are precursors to [[plasticizer]]s.<ref name="Ullmann"/>

In principle, [[1-Hexene|1-hexene]] could be converted to 1-hexanol by [[hydroboration]] ([[diborane]] in [[tetrahydrofuran]] followed by treatment with [[hydrogen peroxide]] and [[sodium hydroxide]]):

[[Image:Hexene-hexanol.png|center]]
[[File:Hexan-1-ol.jpg|thumb|Hexan-1-ol]]

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from [[ethylene]].