Ammonium Chloride → 1-(4-Benzyloxyphenyl)-1-(4-methoxyphenyl)-2-phenylethene

Participants

Reaction Steps

To the Grignard reagent prepared from 1.52 g (63 mg-atom) Mg turnings and 13.45 g (9 mL, 72 mmol) 4-bromoanisole (initiated with one I2 crystal and one drop EtBr2) in 25 mL THF was added 3 g (9.9 mmol) of Benzyl 4-benzyloxyphenyl ketone, prepared in Example 3. The reaction mixture was stirred at reflux for 48 h and then treated with 10 mL aqueous NH4Cl. After cooling to room temperature, the slurry was filtered, the filter cake washed with 50 mL THF, and the filtrates concentrated to give an orange oil. The oil was chromatographed over 60 g flash SiO2 (petroleum ether followed by Me2CO). The Me2CO fractions were combined, concentrated, dissolved in 100 mL 1:1 95% EtOH-2N H2SO4, and refluxed with stirring for 8 h. The solvents were removed to give a brown gum, which was dissolved in 100 mL Et2O, washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL), and H2O (100 mL). The organic layer was dried (MgSO4), filtered, and concentrated to give a brown oil. The oil was purified on 60 g flash SiO2 (9:1 petroleum ether-CH2Cl2) to give 3.1 g of 1-(4-Benzyloxyphenyl)-1-(4-methoxyphenyl)-2-phenylethene (80%) as a clear oil. NMR δ7.41 (brs, 5H, O-benzyl C6H5), 7.3 to 6.75 (m, 9H, substituted rings' ArH and C=CH), 7.11 (s, 5H,=C--C6H5), 5.05 (s, 2H, OCH2Ph), 3.79 (s, 3H, OCH3).

Provenance & Evidence