1-Hexanol

1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. 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 C6H13OH. It is used in the perfume industry. == Preparation == Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. An idealized synthesis is shown: Al(C2H5)3 + 6C2H4 → Al(C6H13)3 Al(C6H13)3 + 1+1⁄2O2 + 3H2O → 3HOC6H13 + Al(OH)3 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 C6-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. == Occurrence in nature == 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. == See also == Cis-3-Hexenal, another volatile organic compound, is also considered responsible for the freshly mowed grass odor. == References == == External links == International Chemical Safety Card 1084