Dibutylamine → N,N-di-n-butyl-3,5-di-t-butyl-4-hydroxybenzamide

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Reaction Steps

To a stirred solution of 25 grams (0.1 mole) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 12.9 grams (0.1 mole) of di-n-butylamine in 100 milliliters of dry tetrahydrofuran was added dropwise a solution of 20.6 grams (0.1 mole) of dicyclohexylcarbodiimide in 75 milliliters of dry tetrahydrofuran. The mixture was stirred for several hours and the white solid (dicyclohexyl urea) was filtered off and discarded. Evaporation of the filtrate gave a white solid, which was recrystallized from 1:1 benzene-hexane to give N,N-di-n-butyl-3,5-di-t-butyl-4-hydroxybenzamide; melting point 94°-95°C. When tested by the procedure of Example 2, the sample containing this compound lasted 1000 hours, about 3.3 times as long as the control.

Provenance & Evidence