Bromobenzene → 1-Pentadecyl-3-phenoxybenzene

Participants

Reaction Conditions

Reaction Steps

Into a 1000 mL round bottom flask containing potassium salt of 3-pentadecyl phenol (111.0 g, 0.32 mol) was added bromobenzene (50.88 g, 0.32 mol) followed by Cu powder (2.22 g, 2 wt %) and DMAc (150 mL). The reaction mixture was heated at 150° C. for 6 h. After completion of the reaction, the obtained dark colored reaction mixture was poured into water (500 mL); the Cu salts were removed by filtration. The filtrate was extracted with ethyl acetate (2×300 mL), washed with saturated aqueous sodium chloride solution (2×100 mL) followed by water (3×100 mL) and dried over sodium sulfate. Solvent evaporation yielded crude 1-pentadecyl-3-phenoxybenzene. Pure 1-pentadecyl-3-phenoxybenzene was obtained after silica gel (60-120 mesh) column chromatography (eluent: pet ether). Yield 70 g (57%); MP 32° C.

Provenance & Evidence