Reaction #65001

Reaction equation

2,6-di(tertiary-butyl)-p-benzoquinone

4-aminobenzoic acid

boron trifluoride

→

2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturediethyl ether complex was heated on a steam bath for 1.25 hours
2. 2
   OtherEvaporation
3. 3
   Otherprovided a solid which
4. 4
   Washwas washed with hexane
5. 5
   Otherrecrystallized from ethanol

Procedure

A mixture of 22 g (0.10 mole) of 2,6-di(tertiary-butyl)-p-benzoquinone, 13.7 g (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.

Source