Water → HCID 890054, compound

Participants

Reaction Steps

To a solution of 4′-hydroxy-2′-methylacetophenone (3.06 g, 20 mmol) in N,N-dimethylformamide (20 mL), potassium carbonate (3.66 g, 26.4 mmol), benzyl bromide (2.7 mL, 22.4 mmol) and n-Bu4NI (0.75 g, 2.03 mmol) were added and stirred at room temperature for 14 hours. The reaction mixture was diluted with saturated aqueous ammonium chloride under ice cooling, followed by addition of water and ethyl acetate to separate the organic layer. The organic layer was washed with 20 wt. % aqueous sodium thiosulfate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1→6:1) to give the titled compound (5.05 g, quant.) as a colorless powder.

Provenance & Evidence