In a
500-ml. three-necked round-bottomed flask equipped with a
sealed stirrer, a
reflux condenser, and a
dropping funnel are placed
36 g. (0.45 mole) of ethylene chlorohydrin (Note
1),
5 ml. of concentrated sulfuric acid, and
35 ml. of benzene. The mixture is warmed on a
water bath, and to it is added, with efficient stirring, a solution of
55 g. (0.30 mole) of benzhydrol (Note
2) in
65 ml. of benzene (Note
3) during 30–50 minutes. The reaction mixture is heated at the reflux temperature for an additional 4 hours with stirring. To the cooled mixture is added about
35 ml. of benzene, and the combined
benzene layer is washed with water and dried over
calcium chloride. The drying agent is removed, the
benzene is evaporated, and the residue is distilled under reduced pressure. The
benzhydryl β-chloroethyl ether is collected at
144–148°/1.0 mm. (
174–177°/4 mm.) as a colorless, viscous oil,
n30D 1.5651, which should be removed from the
receiver to a
beaker or Erlenmeyer flask immediately after the distillation. The oil solidifies to a hard white mass, m.p.
27.4–27.8°, when kept in an ice chest (Note
4). The yield is
60.0–65.3 g. (
81–88%).