Organic Syntheses, CV 1, 144
Submitted by James F. Norris and Alanson W. Olmsted.
Checked by Henry Gilman and L. L. Heck.
1. Procedure
In a
500-cc. separatory funnel are placed
74 g. (95 cc., 1 mole) of tert.-butyl alcohol (Note
1) and
247 cc. (3 moles) of c.p. concentrated hydrochloric acid (sp. gr. 1.19). After shaking, the layers are allowed to separate (fifteen to twenty minutes) and the upper layer is drawn off and washed first with a
5 per cent sodium bicarbonate solution, then with water until neutral to moist litmus paper (Note
2) and (Note
3). The chloride is treated with
10 g. of calcium chloride and shaken thoroughly, then transferred to a
125-cc. distilling flask. It is then distilled, using a
long water condenser. The fraction boiling at
49.5–52° weighs
72–82 g. (
78–88 per cent of the theoretical amount).
2. Notes
1. As it is difficult to prepare
tert.-butyl alcohol free from water,
84 g. of the constant-boiling mixture of the alcohol and water can be used. This mixture boils at 80°, contains
88.24 per cent alcohol when the distillation is carried out at 760 mm., and can be readily obtained by distilling a sample of the dilute alcohol.
2. The chloride is very slowly hydrolyzed by cold water.
3. Discussion
This preparation is referenced from:
Copyright © 1921-2002, Organic Syntheses, Inc. All Rights Reserved