In a
2-l. flask provided with a
reflux condenser and a
dropping funnel is placed
380 g. (5.2 moles) of diethylamine (b.p.
52–60°). The
diethylamine is heated to boiling over a
steam bath, and
320 g. (4 moles) of ethylene chlorohydrin is added from the dropping funnel during the course of about one hour. Heating is then continued for eight hours more. The reaction mixture is allowed to cool, and a solution of
230 g. of sodium hydroxide in 350 cc. of water is added fairly rapidly with constant shaking. Two layers form immediately, and
sodium chloride is precipitated. The latter is dissolved by the addition of 400 cc. of water, and then
500 cc. of benzene is added and the mixture is stirred mechanically for five minutes. The
benzene layer is separated and the aqueous layer is extracted three times more,
500 cc. of benzene being used for each extraction. The combined
benzene extracts are dried over about
100 g. of solid potassium carbonate, with mechanical stirring until the turbidity of the solution has disappeared. The solution is distilled from a
3-l. flask provided with a
50-cm. column (packed with glass or Carborundum) and a
thermometer dipping in the liquid. Distillation is continued until the temperature of the liquid reaches 100° and that at the top of the column is 85°. The residue is transferred to a
1-l. Claisen flask having a 30-cm. column, and is distilled under reduced pressure. Cuts are taken at 45°/20 mm., 45–64°/18 mm., and 64–65°/18 mm. The last fraction amounts to about
290 g. The first two fractions are redistilled and more
β-diethylaminoethyl alcohol is obtained (Note
1). The total yield is
320–330 g. (
68–70 per cent of the theoretical amount).