3-Aminobenzoic Acid → 3-(3,5-DI-T-Butyl-4-hydroxyanilino)benzoic acid

Participants

Reaction Steps

A mixture of 6.6 g of 2,6-di-tert-butyl-1,4-benzoquinone, 4.2 g of m-aminobenzoic acid and 6 drops of acetic acid was stirred with heating at a temperature of 150°-160° C. for 2 hours and then allowed to cool. To the reaction mixture were added about 50 ml of water and then 200 ml of THF. Further a solution of 50 g of Na2S2O4 in 300 ml of water was also added to the red mixture at room temperature, and the mixture was stirred for about 15 minutes until a decoloration took place. Then the mixture was poured into water and extracted with ethyl acetate. The organic layer was treated in the same manner as in Example 1 and the resulting crude product was purified by silica gel column chromatography (eluent: CH2Cl2 -THF=5:1), giving 6.7 g of the title compound. The title compound will be referred to as "Compound 24."

Provenance & Evidence