Ethylene Glycol → N-methyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-trifluoromethylaniline

Participants

Reaction Conditions

Reaction Steps

N-Methyl-N-(2,2-dimethoxyethyl)-2,6-dinitro-4-trifluoromethylaniline (3.2 grams; 0.0915 mole), ethylene glycol 0.57 grams; 0.0915 mole), para-toluenesulfonic acid (200 mg) and ethyl acetate were charged into a glass reaction vessel equipped with a stirrer, heating mantle, reflux condenser and thermometer. The reaction mixture was heated at 120° C. with stirring for one hour. After this time the mixture was cooled to room temperature and washed with aqueous sodium bicarbonate. The washed solution was dried over anhydrous sodium sulfate, filtered and stripped of solvent leaving a solid residue. The residue was recrystallized from hexane to yield the desired N-methyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-trifluoromethylaniline as a yellow crystalline solid melting at 83° C.

Provenance & Evidence