1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C<sub>6</sub>H<sub>13</sub>OH. It is used in the perfume industry.
Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. An idealized synthesis is shown:
The process generates a range of oligomers that are separated by distillation.
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 plasticizers.
In principle, 1-hexene could be converted to 1-hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide):
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.
1-Hexanol is believed to be a component of the odour of freshly mown grass. Alarm pheromones emitted by the Koschevnikov gland of honey bees contain 1-hexanol. It also is partly responsible for the fragrance of strawberries.