Water → HCID 68873227, compound

Participants

Reaction Steps

To a solution of methyl 4-(4-ethylbenzyl)-3-hydroxybenzoate (1.3 g) in N,N-dimethylformamide (15 mL) were added potassium carbonate (0.79 g) and benzyl bromide (0.62 mL), and the mixture was stirred at room temperature for 13 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in diethyl ether (10 mL), and the solution was added to a suspension of lithium aluminum hydride (0.57 g) in diethyl ether (50 mL) at 0° C. The mixture was heated under reflux for 1.5 hours. After cooling to 0° C., to the reaction mixture was successively added water (0.60 mL), 15% aqueous sodium hydroxide solution (0.60 mL) and water (1.8 mL), and the mixture was stirred for 5 minutes. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give 3-benzyloxy-4-(4-ethylbenzyl)benzyl alcohol (1.3 g).

Provenance & Evidence