Organic Syntheses, CV 2, 28
Submitted by J. C. Eck
Checked by Louis F. Fieser and C. H. Fisher.
1. Procedure
In a
500-cc. round-bottomed flask,
50 g. (0.44 mole) of 2-ketohexamethylenimine (p. 371) is added to a solution of
45 cc. of concentrated hydrochloric acid (sp. gr. 1.19) in 150 cc. of water. The solution is boiled for about one hour until it becomes clear (Note
1) and evaporated to dryness under reduced pressure on a
steam bath.
After the complete removal of halogen and metallic ions, the solution is concentrated to a volume of about 100 cc., and
300 cc. of absolute alcohol is added. Then the amino acid is precipitated by slowly adding
500 cc. of ether with stirring and cooling.
The resulting
ε-aminocaproic acid is collected on a
suction filter and dried in a
desiccator. The yield of
ε-aminocaproic acid melting at
201–203° is
52.5–53.5 g. (
90–92 per cent of the theoretical amount).
2. Notes
1. This indicates that the hydrolysis is complete.
2. The exact amount of
silver oxide required may be determined by titrating a sample of the solution with
silver nitrate by the Volhard method.
3. Discussion
This preparation is referenced from:
Copyright © 1921-2002, Organic Syntheses, Inc. All Rights Reserved