Caprolactam → hexanoic acid, 6-amino-, monosodium salt

反応式

[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)CCCCC(Cl)=[O:15].[OH-].[Na+:20]>>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O-:8])=[O:15].[Na+:20]

参加物

反応物 3

HCID 7768Caprolactam

HCID 14798Sodium Hydroxide

HCID 61034Adipoyl chloride

生成物 1

HCID 23663648hexanoic acid, 6-amino-, monosodium salt収率 70%

実験手順

The literature has described various methods for preparation of TOCAP and related compounds. German Patent 949,568 (Kruckenberg) discloses the reaction of caprolactam with various acyl halides including adipoyl dichloride in the presence of sodium hydroxide. Once sodium 6-aminocaproate has formed, the reactor is charged with a first portion acyl halide, sodium hydroxide and then a final portion acyl halide. A related method is reported by Zinner et al in J. Prakt. Chem. 17, 147-153 (1962). The procedure requires the addition of all the sodium hydroxide to be charged to the reaction vessel at the beginning of the synthesis. The reported yield is 70% of theory.