Benzyl Bromide → (((10-Bromodecyl)oxy)methyl)benzene

Participants

Reaction Steps

10-Bromodecan-1-ol (4.6 g) was dissolved in 20 ml of dried THF, and sodium hydride (933.6 mg) was added to this solution. The reaction mixture was stirred at room temperature for 30 minutes, then benzyl bromide (2.78 ml) was added using a syringe, and the reaction mixture was refluxed for 24 hours while stirring. Saturated ammonium chloride solution was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane:dichloromethane=8:2) gave 1-((10-bromodecanoxy)methyl)benzene as a colorless oil at an 88% yield.

Provenance & Evidence