Glycerol → Quinoline, 8-ethyl-

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-ethylaniline (24.2 g, 200 mmol) and sodium iodide (0.40 g, 2.67 mmol) in 80% sulfuric acid (110 g) at 140° C. was added glycerine (22.0 g, 239 mmol) over a period of 30 m. The reaction mixture was stirred at 140-145° C. for 3 hours in an apparatus fitted with a Dean Stark trap. The reaction mixture was cooled to room temperature. The mixture was neutralized with 25% NaOH (aq) (210 g) to pH 7, and diluted with toluene. The mixture was extracted with ethyl acetate/ether. The pooled organic layers were washed with brine, and dried over magnesium sulfate. The mixture was filtered, to and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 5 to 7% ethyl acetate in hexane to give 8-ethylquinoline (12) (24.5 g, 156 mmol, 78% yield).

Provenance & Evidence