Benzyl Alcohol → HCID 13198832, compound

Participants

Reaction Steps

To a solution of trans-1,4-dibromobut-2-ene (20.0 g, 93.5 mmol), benzyl alcohol (10.6 mL, 102.9 mmol), and tetrabutylammonium hydrogensulfate (3.17 g, 9.35 mmol) in dichloromethane (80 mL) were added sodium hydroxide (33.7 g, 841 mmol) in water and the resulting mixture was stirred at room temperature for 24 hours. It was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography to yield 10.8 g of trans-4-benzyloxy-1-bromo-2-butene; 1H NMR (400 MHz, CDCl3) δ ppm 3.98 (d, 2H, J=7.3 Hz) 4.04 (d, 2H, J=4.4 Hz) 4.54 (s, 2H) 5.82-6.08 (m, 2H) 7.25-7.45 (m, 5H).

Provenance & Evidence