4-Methoxybenzyl alcohol (1 eq.) and bromoacetic acid (1.2 eq.) were dissolved in anhydrous tetrahydrofuran at 0 °C. Sodium hydride (60% w/w, mineral oil dispersion, 3 eq.) was added in three batches. The reaction mixture was stirred at 70 °C for 4 hours. After cooling to room temperature, water was added and the resulting mixture was washed with hexane. The aqueous phase was acidified to pH 2 with 1N hydrochloric acid and subsequently extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography with hexane solution of 50% ethyl acetate as eluent gave (4-methoxybenzyloxy)acetic acid (0.51 g, 71% yield) as a colorless solid.1H NMR (500 MHz, CDCl3) δ 7.29 (m, 2H), 6.90 (m, 2H), 4.59 (s, 2H), 4.10 (s, 2H), 3.81 ( s, 3H).
