1,6-Dibromohexane → 4-((6-Bromohexyl)oxy)-3-chloroanisole

Participants

Reaction Steps

A solution of 29.6 g. (0.74 mole) sodium hydroxide pellets in 400 ml. absolute ethanol was prepared with stirring at room temperature and a solution of 108.0 g. (0.68 mole) 2-chloro-4-methoxyphenol in 200 ml. absolute ethanol was added in a fine stream. The solution was stirred at room temperature for 15 minutes, then warmed gently in a steam bath for one-half hour. The reaction mixture was chilled to about 5° C. in an ice bath and 500 g. (2.05 moles) 1,6-dibromohexane was added. The reaction was stirred and allowed to warm to room temperature, then stirred for 6 hours at room temperature and boiled overnight at reflux.

Provenance & Evidence