Water → 1-(2-Chloroethoxy)-4-(chloromethyl)benzene

Participants

Reaction Steps

10 Grams (0.06 mol) of 4-(2-hydroxyethoxy)benzyl alcohol, prepared according to L. M. Marson, Il Farmaco ed. sci. 14, 159 (1959)), was dissolved in anhydrous pyridine (80 ml) and anhydrous chloroform (100 ml), then the mixture was ice cooled and thionyl chloride (80 ml) was slowly added, under stirring. Stirring was continued, allowing temperature to raise to the room's one, then the mixture was heated for about 2 hours to complete the reaction. After cooling, the reaction mixture was poured into water (200 ml); the chloroformic layer was separated, washed with a 5% aqueous solution of sodium hydroxyde, dried over Na2SO4 and evaporated. The residue was distilled under vacuum to provide the pure product (8.2 g; 66.6% yield).

Provenance & Evidence