Hydrochloric Acid → HCID 18470383, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60%, 0.39 g) was added to a mixture of 6-bromohexanol (1.78 g) and 4-chlorobenzyl bromide (2.02 g) in dry tetrahydrofuran (150 ml). The mixture was stirred at 25° C. for 5 h and poured into 1M hydrochloric acid. Extraction with diethyl ether (3×), and washing the combined extracts with water and brine gave a solution that was dried over magnesium sulfate and evaporated under reduced pressure. The residue so obtained was chromatographed on silica gel using 40-60° C. petroleum ether to 10% diethyl ether in 40-60° C. petroleum ether as eluents. This gave 1-bromo-6-(4-chlorobenzyloxy)hexane (1.7 g). 1H-NMR (CDCl3) δ 1.3-1.55 (4H, m), 1.55-1.7 (2H, m), 1.75-1.95 (2H, m), 3.35-3.55 (4H, m), 4.46 (2H, s) and 7.2-7.4 (4H, m).

Provenance & Evidence