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

Participants

Reaction Steps

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 to give, in a yield of 78% of theory, 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.), catalytic hydrogenation of which, in the presence of platinum dioxide, gives amorphous 2,3-diamino-1-(2-hydroxy-3-tert.-butylaminopropoxy)-4-methylbenzene trihydrochloride.

Provenance & Evidence