O-Xylene → N-(4-anilinophenyl)-2-hydroxyisobutyramide

Participants

Reaction Steps

A 500 milliliter resin pot was charged with 52 grams (0.05 moles) of α-hydroxy isobutyric acid from Example 1, 77.3 grams (0.42 moles) p-aminodiphenylamine, 1 gram p-toluene sulfonic acid and 140 mls. of xylene under a nitrogen blanket. A Dean-Stark water separator and a condenser was attached to the resin pot and the mixture was heated to vigorous reflux with H2O being removed as it was formed. After 3 hours of reflux the heat was removed and the product was allowed to crystallize in the resin pot under nitrogen. The product was broken up, washed with toluene, filtered and dried to obtain 104.4 grams (92% yield) of N-(4-anilinophenyl)-2-hydroxyisobutyramide with a melting point of 171°-174° C.

Provenance & Evidence