4-Aminobenzoic Acid → 2,6-Di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-l-one

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Reaction Conditions

Reaction Steps

A mixture of 22 g (0.10 mole) of 2,6-di(tertiary-butyl)-p-benzoquinone, 13.7g (0.10 mole) of 4-aminobenzoic acid, 175 ml of tetrahydrofuran and 1 ml of boron trifluoride: diethyl ether complex was heated on a steam bath for 1.25 hours. The mixture was allowed to cool to about 20° C. over 16 hours under a nitrogen atmosphere. Evaporation provided a solid which was washed with hexane and recrystallized from ethanol to provide orange solid 2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one, m.p. 305°-309° C. Analysis: Calculated for C21H25NO3 : %C, 74.3; %H, 7.4; %N, 4.1; Found: %C, 74.2; %H, 7.4; %N, 4.1.

Provenance & Evidence