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Relevant academic research and scientific papers

A KINETIC STUDY OF CYCLODEHYDRATION OF β-(p-TOLUIDINO)ACROLEIN. II. SULFONATION OF THE AROMATIC RING AS A SIDE REACTION OF CYCLODEHYDRATION IN SULFURIC ACID

Sulfonation of the benzene ring of 3-(p-toluidino)-1-oxo-2-propene-2-sulfonic acid (III) (6.11x1E-5 M) in 99.4percent sulfuric acid at 25 deg C was observed by following the UV spectral change of the solution.In a 9.51x1E-1 M solution in 99.4percent sulfuric acid, however, the bulk of III remained unchanged, and on dilution with 93.8percent sulfuric acid, 6-methylquinoline (II) was formed.Sodium 4-(3-oxo-1-propenylamino)benzenesulfonate (V), sodium 4-(3-oxo-1-propenylamino)-3-methylbenzenesulfonate (VI) and sodium 2-(3-oxo-1-propenylamino)-5-methylbenzenesulfonate (VII) were synthesized in connection with this investigation.Keywords - sulfonation; cyclodehydration; 6-methylquinoline; β-(p-toluidino)acrolein; sodium 4-(3-oxo-1-propenylamino)benzenesulfonate; sodium 4-(3-oxo-1-propenylamino)-3-methylbenzenesulfonate; sodium 2-(3-oxo-1-propenylamino)-5-methylbenzenesulfonate; sodium 2-(2-formyl-3-hydroxy-5,5-diethoxy-1-pentenylamino)-5-methylbenzenesulfonate.