5-гексен-1-ол

Химические свойства

Clear, colorless liquid with a green aroma.

Использование

5-Hexen-1-ol is used in cyclization to a tetrahydropyran by phenylselenoetherification. It is also used as a building block in synthetic chemistry. Further, it is used to prepare 6-bromo-hex-1-ene by reaction with phosphorus tribromide.

Подготовка

5-hexen-1-ol may be prepared from 2-(chloromethyl)tetrahydropyran according to the literature procedure for the preparation of 4-penten-1-ol (Brooks, L. A.; Snyder, H. R. Org. Synth. Coll. Vol. III 1955, 698).

прикладной

5-Hexen-1-ol is used as a food flavouring agent and as a raw material in organic synthesis for cyclisation to other compounds such as tetrahydropyran via phenylselenide etherification.

Пороговое значение запаха

Medium strength odor; recommend smelling in a 10.00% solution or less

Синтез

6-bromo-1-hexene is used as a raw material, and tetrabutylammonium bromide is used as a catalyst. In an acetonitrile solvent, it is heated to react with potassium acetate. The mixed solution is then cooled to room temperature (18-25°C), the reaction solution is concentrated under reduced pressure, and then water is added to dissolve; methyl tert-butyl ether is added and stirred to separate the layers, the water layer is extracted once with methyl tert-butyl ether, the organic phases are combined and filtered, and the filtrate is concentrated under reduced pressure. The concentrated solution begins to hydrolyze, and 15% alkaline aqueous solution and methanol are added to the concentrated solution. The mixture is stirred at room temperature to dissolve each other; after the hydrolysis is completed, the methanol is concentrated under reduced pressure. After concentration to dryness, the system begins to separate into layers, with an upper organic phase and a lower aqueous phase. The aqueous phase is extracted twice with dichloromethane, and the combined organic phases are concentrated under reduced pressure to obtain 5-Hexen-1-ol.