Benzyl Bromide → Benzyl glycidyl ether

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% oil dispersion, 23.6 g, 0.59 mol) was added in portions to a solution of glycidol (14) (40 g, 0.54 mol), benzyl bromide (101.5 g, 0.59 mol), and n-butylammonium iodide (0.24 g) in dry DMF (150 mL) at 25° C. (Step 12). The mixture was stirred for 1 hr at 65° C., poured over ice and then extracted with ether (2×75 mL). The combined ether extract was washed with water (3×75 mL) and dried over MgSO4. Distillation using a 12-in vigreux column afforded 62.9 g (71%) of glycidyl ##STR7## benzyl ether 15; bp 120°-122° C. (10 mm); 1H NMR (CDCl3) δ 2.6 (dd, 1H, OCHa), 2.8 (dd, 1H, OCHb), 3.2 (m, 1H, OCHc), 3.2 (dd, 1H, OCHd), 3.8 (dd, 1H, OCHe), 4.6 (dd, 2H, OCH2), 7.23 (s, 5H, phenyl).

Provenance & Evidence