Ethylparaben → HCID 59504711, compound

Participants

Reaction Steps

To a solution of ethyl 4-hydroxybenzoate (2.0 g, 12.04 mmol) in dry DME (50 mL) was added potassium carbonate (3.33 g, 24.07 mmol), potassium iodide (100 mg, 0.602 mmol) and 1-bromo-2-(2-methoxyethoxy)ethane (3.6 mL, 24.07 mmol). The mixture was stirred at reflux for 2 days. After being cooled to rt, the solids were removed by filtration and the solvent by evaporation in vacuo. The remaining crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 5:1) to afford the title compound (2.17 g, 67%): 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 2H), 6.93 (d, 2H), 4.33 (quart, 2H), 4.19 (t, 2H), 3.88 (t, 2H), 3.72 (t, 2H), 3.57 (t, 2H), 3.39 (s, 3H), 1.37 (t, 3H); DCI(NH3)-MS m/z 286 (M+NH4)+; HPLC RT (Method I) 4.14 min.

Provenance & Evidence