1-Bromo-3-chloropropane → 3-(2-Naphthyloxy)-1-chloropropane

Participants

Reaction Steps

A mixture of 2-naphthol (72.07 g, 0.5 mol), 1-chloro-3-bromopropane (78.72 g, 0.5 mol), and potassium carbonate (103.65 g, 0.75 mol) was heated at reflux 16 hr in 750 mL of acetone. The mixture was cooled to room temperature and filtered. The reaction was concentrated to a viscous oil using a rotary evaporator. The oil was dissolved in chloroform and washed with 5% sodium hydroxide and water. The chloroform was dried (Na2SO4) and filtered. Chloroform was removed to give a brown solid. A ten-gram sample was subjected to flash chromatography on silica gel using 2% ethyl acetate-hexanes, 3% ethylacetate-hexanes, 5% ethyl acetate-hexanes, and 10% ethyl acetate-hexanes for elution. Fractions of similar purity were combined and solvents removed. A clear oil was obtained and dried 16 hr at 80° C. A white crystalline solid was formed on standing at room temperature. This procedure provided 7.01 g (52.2%) of white crystalline solid, mp 46°-49° C.

Provenance & Evidence