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

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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. 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.

Provenance & Evidence