Epichlorohydrin → 2-[(4-Methyl-2,3-dinitrophenoxy)methyl]oxirane

反応式

[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[CH:7]=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].Cl[CH2:16][CH:17]1[O:19][CH2:18]1.[OH-].[Na+]>>[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[CH:7]=[CH:6][C:5]=1[O:14][CH2:16][CH:17]1[O:19][CH2:18]1)([O-:3])=[O:2]

参加物

反応物 3

HCID 7835Epichlorohydrin

HCID 14798Sodium Hydroxide

HCID 50098Dinitrocresols

生成物 1

HCID 129266502-[(4-Methyl-2,3-dinitrophenoxy)methyl]oxirane収率 78%

実験手順

2,3-Dinitro-4-methylphenol (see H. E. Dadswell and J. Kenner, J. Chem. Soc., 1927, 583) is reacted with 3-chloro-1,2-epoxypropane and 25% aqueous sodium hydroxide solution. There is obtained, in 78% yield, 2,3-dinitro-1-(2,3-epoxypropoxy)-4-methylbenzene; m.p. 121°-123° C. This compound is reacted in boiling ethanol with tert.-butylamine to give 2,3-dinitro-1-(2-hydroxy-3-tert.-butylaminopropoxy)-4-methylbenzene; m.p. 104°-106° C. By catalytic hydrogenation over platinum dioxide, there is obtained therefrom amorphous 2,3-diamino-1-(2-hydroxy-3-tert.-butylaminopropoxy)-4-methylbenzene in the form of its trihydrochloride.