Hydrochloric Acid → HCID 15599097, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a mixture of 2.97 g (0.01 mole) of 4-anilino-2,6-di-t-butylphenol and 4.90 g 0.05 mole) of maleic anhydride was heated at 140° C. for 2 hours. The cooled reaction mixture was suspended in 10% sodium hydroxide, and was then acidified with 10% hydrochloric acid. The resulting precipitate was collected, rinsed with water, air dried, and recrystallized from a mixture of ethyl acetate and hexane to give a yellow solid. This material was dissolved in hot ethanol. The ethanol solution was acidified with 6N hydrochloric acid, and then saturated with water. The resulting precipitate was collected, rinsed with water and air dried. This material was purified by silica gel chromatography, eluting with ethyl acetate, followed by recrystallization from a mixture of ethyl acetate and hexane to give 0.5 g of yellow crystalline N-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenylmaleamic acid, m.p. 154°-157° C. Analysis: Calculated for C25H29NO4 :% C, 72.9; % H, 7.9; % N, 3.5. Found: % C, 73.2; % H, 7.7; % N, 3.3.

Provenance & Evidence