Acetic Anhydride → 4,4'-Methylenebis[2,6-diethylaniline]

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Reaction Steps

in N-methylpyrrolidone (350 ml) was added 5,5'[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]-bis-1,3-isobenzofurandione (67.27 g, 0.1515 mol) under an inert atmosphere at room temperature. The resulting viscous orange solution was stirred overnight at room temperature. A solution of acetic anhydride (61.25 ml, 0.60 mol) and triethylamine (60.71 ml, 0.60 mol) was added with rapid stirring at room temperature. After stirring for 3 hours, the solution was diluted with additional N-methylpyrrolidone and precipitated in water. The resulting solid was collected and washed twice with water, washed twice with methanol, and allowed to air dry. The solid was further dried in a vacuum oven at 20 inches (0.51 m) mercury and 100° C. for 15 hours and at 245° C. for 4 hours to yield 99.4 g product.

Provenance & Evidence