Reacción #7472

Ecuación de reacción

sodium hydroxide

4-hydroxybenzaldehyde

cesium carbonate

cyclobutyl bromide

→

4-cyclobutyloxybenzaldehyde

Rendimiento 75.1%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with diethyl ether
2. 2
   LavadoThe organic layer was washed with 0.5 mol/L aqueous sodium hydroxide solution, water and brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   OtroThe solvent was removed under reduced pressure

Procedimiento

To a suspension of 4-hydroxybenzaldehyde (0.12 g) and cesium carbonate (0.49 g) in N,N-dimethylformamide (2 mL) was added cyclobutyl bromide (0.15 g), and the mixture was stirred at 65° C. overnight. To the reaction mixture was added 1 mol/L aqueous sodium hydroxide solution, and the mixture was extracted with diethyl ether. The organic layer was washed with 0.5 mol/L aqueous sodium hydroxide solution, water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-cyclobutyloxybenzaldehyde (0.13 g). To a solution of the obtained 4-cyclobutyloxybenzaldehyde (0.13 g) in methanol (10 mL) was added sodium borohydride (0.056 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1 mol/L hydrochloric acid solution, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 4-cyclobutyloxybenzyl alcohol (0.12 g).

Fuente