Org. Synth. 1934, 14, 28
DOI: 10.15227/orgsyn.014.0028
β-DIETHYLAMINOETHYL ALCOHOL
[Ethanol, 2-diethylamino-]
Submitted by W. W. Hartman
Checked by W. H. Carothers and W. L. McEwen.
1. Procedure
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).
2. Notes
1.
The physical properties of
β-diethylaminoethyl alcohol are described in detail by Headlee, Collett, and Lazzell.
1
3. Discussion
β-Diethylaminoethyl alcohol has been prepared by reduction of
diethylaminoacetic ester with
sodium and
alcohol;
2 by the action of
ethylene chlorohydrin on
diethylamine;
3 by the action of
ethylene oxide on
diethylamine;
1 and from
ethanolamine and
ethyl sulfate.
4
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
diethylaminoacetic ester
alcohol (64-17-5)
potassium carbonate (584-08-7)
Benzene (71-43-2)
sodium hydroxide (1310-73-2)
sodium chloride (7647-14-5)
sodium (13966-32-0)
Ethylene oxide (75-21-8)
ethylene chlorohydrin (107-07-3)
diethylamine (109-89-7)
ethanolamine (141-43-5)
β-Diethylaminoethyl alcohol,
Ethanol, 2-diethylamino- (100-37-8)
ethyl sulfate
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