(Z)-6-Nonen-1-ol, also known as cis-6-Nonen-1-ol, is a colorless transparent liquid at room temperature and pressure, with a unique aroma. It is soluble in water and most organic solvents, including low-polarity ether solvents. (Z)-6-Nonen-1-ol is a type of olefinic alcohol compound, commonly used as an intermediate in organic synthesis and the production of flavors and fragrances. It finds applications in the field of basic research in organic synthesis methods and the production of cold drinks and candies.

Chemical Properties

The olefin unit in the structure of (Z)-6-Nonen-1-ol exhibits high chemical reactivity, undergoing various electrophilic addition reactions. It can react with halogens to undergo electrophilic addition reactions, as well as undergo epoxidation in the presence of oxidants or ozonolysis to produce corresponding aldehyde derivatives. (Z)-6-Nonen-1-ol can also undergo hydrogenation reactions to yield the corresponding alkyl alcohol derivatives.

Esterification Reaction

Figure 1: (Z)-6-Nonen-1-ol esterification reaction

In a dry reaction flask, (Z)-6-Nonen-1-ol (10.0 mmol, 1.56 g, 1.0 equivalent) and TsCl (12.0 mmol, 2.29 g, 1.2 equivalents) are dissolved in dry dichloromethane (30 mL) under an argon atmosphere. Et3N (13.0 mmol, 1.32 g, 1.3 equiv) and DMAP (1.00 mmol, 122.2 mg, 0.10 equiv) are slowly added to the reaction mixture. The resulting mixture is stirred at room temperature for about 6 hours, monitored by TLC for reaction progress. After the reaction, it is quenched with saturated NH4Cl aqueous solution, then extracted with DCM (3×30 mL). The organic layer is washed with water and brine, dried over anhydrous Na2SO4, filtered, concentrated under vacuum, and the residue is purified by silica gel column chromatography to obtain the target product molecule.[1]

Chemical Applications

Due to its structural diversity, (Z)-6-Nonen-1-ol is used as an intermediate in organic synthesis, introducing olefin and alcohol functional groups to generate various complex compounds, widely employed in pharmaceutical and fine chemical synthesis. In the field of flavors and fragrances, (Z)-6-Nonen-1-ol serves as a food flavor additive, with its odor characteristics and chemical reactivity making it an important component in fragrance synthesis.

References

[1] Snyder, Scott A.; et al, Journal of the American Chemical Society, 2011, 133, 15898-15901.