Glycerol → Quinoline, 8-ethyl-

Temperature

142.5 °C

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).

1. customfitted with a Dean Stark trap
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionThe mixture was extracted with ethyl acetate/ether
4. washThe pooled organic layers were washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationThe mixture was filtered
7. customto and the solvents were removed under vacuum
8. customThe residue was purified by chromatography on silica gel with 5 to 7% ethyl acetate in hexane

ORD record

ord-c06d6d11352a4912842efa879e09d7c3

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119807B2