Acetic Acid → O-Ethylacetanilide

Temperature

120 °C

2-Ethylaniline (9.70 g, 80.0 mmol) was added to a mixture of glacial AcOH (30 mL) and acetic anhydride (20 mL), and the resulting mixture was refluxed at 120° C. for 3 h. The reaction mixture was then cooled to room temperature and poured into a boiling mixture of water and EtOH (20 mL each). The mixture was stirred at rt for 1 h and then cooled (0-5° C.) overnight. EtOH was evaporated and the remainder of the mixture was diluted with water (100 mL). The obtained mixture was neutralized with Na2CO3 and extracted with EtOAc. The combined extract was washed with brine, dried with anhydrous MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with 5% MeOH in CH2Cl2, to afford 5.50 g (42%) of the title compound as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 9.25 (broad s, 1H), 7.05-7.40 (m, 4H), 2.55 (q, J=7.6 Hz, 2H), 2.02 (s, 3H), 1.09 (t, J=7.6 Hz, 3H).

1. temperatureThe reaction mixture was then cooled to room temperature
2. temperaturecooled (0-5° C.) overnight
3. customEtOH was evaporated
4. additionthe remainder of the mixture was diluted with water (100 mL)
5. extractionextracted with EtOAc
6. extractionThe combined extract
7. washwas washed with brine
8. dry with materialdried with anhydrous MgSO4
9. filtrationfiltered
10. customevaporated
11. customThe residue was purified by chromatography on silica gel eluting with 5% MeOH in CH2Cl2

ORD record

ord-8b2397de44e64fecb4d3758850641ba8

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633186B2