反应详情

Sodium hydride (2.4 g, 0.1 mol) was suspended in 150 mL dry glyme. Monobenzylhydroquinone (20.0 g, 0.1 mol) was dissolved in 250 mL dry glyme and added dropwise to the sodium hydride suspension with stirring under nitrogen at room temperature. 1-Bromohexane (16.5 g, 0.1 mol) was added dropwise and the reaction mixture was refluxed for 1 day. The reaction product was cooled and the glyme removed under reduced pressure. The residue was dissolved in 300 mL 1:1 ethanol-ethyl acetate and catalytically hydrogenated using 2 g 10% Pd on C and a hydrogen pressure of 500 kPa at room temperature for 4 hours. The catalyst was removed by filtration and the solvent was removed from the filtrate under reduced pressure. The crude product residue was recrystallized from aqueous ethanol to yield 15 g 4-hexyloxyphenol.

1. temperaturethe reaction mixture was refluxed for 1 day
2. temperatureThe reaction product was cooled
3. customthe glyme removed under reduced pressure
4. dissolutionThe residue was dissolved in 300 mL 1:1 ethanol-ethyl acetate
5. customThe catalyst was removed by filtration
6. customthe solvent was removed from the filtrate under reduced pressure
7. customThe crude product residue was recrystallized from aqueous ethanol