Sulfuric Acid → 6-Butylquinoline

Participants

Reaction Conditions

Reaction Steps

38.6 (259 mM) of 4-butylaniline, 80.5 g (875 mM) of glycerin, 25.0 g of m-nitrobenzenesulfonic acid, 7.6 g of ferric sulfate and 13.2 g of boric acid were placed in a 500 ml-three necked flask. To the mixture, 47.4 ml of conc. sulfuric acid was added dropwise over 20 minutes with stirring on an ice bath, whereby the temperature was increased from 8° C. to 50° C. The mixture was heat-refluxed at 135-145° C. for 2 hours under stirring. After the reaction, the reaction mixture was poured into ice water and alkalinized with 20% NaOH aqueous solution to pH=11, followed by extraction with toluene. The organic layer was washed with water and evaporated. The residue was purified by silica gel column chromatography (eluent: toluene/THF) to obtain 31.9 g of 6-butylquinoline (yield: 66.6%).

Provenance & Evidence