反应详情

温度

45 °C

Acetyl chloride (0.46 mL, 0.50 g, 6.4 mmol) was added to a solution of 4-oxo-1-phenylcyclohexanecarboxylic acid (Description 17, 0.94 g, 4.3 mmol) in methanol (5 mL) and the mixture was heated under reflux for 20 hours. The mixture was cooled, poured into aqueous sodium hydrogen carbonate (saturated, 100 mL) and extracted with ethyl acetate (2×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (2 mL), acetic acid (6 mL) and water (2 mL) were added and the mixture was stirred at 45° C. for 2 hours. The mixture was cooled, the solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 100 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL), the combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (0.98 g, 98%). 1H NMR (250 MHz, CDCl3) δ 7.45–7.26 (5H, m), 3.72 (3H, s), 2.77 (2H, m), 2.61–2.38 (4H, m), and 2.25 (2H, m).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 20 hours
3. temperatureThe mixture was cooled
4. extractionextracted with ethyl acetate (2×50 mL)
5. dry with materialThe combined organic fractions were dried (Na2SO4)
6. customthe solvent was evaporated under reduced pressure
7. dissolutionThe residue was dissolved in tetrahydrofuran (2 mL)
8. additionacetic acid (6 mL) and water (2 mL) were added
9. temperatureThe mixture was cooled
10. customthe solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 100 mL)
11. additionwas added
12. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
13. dry with materialthe combined organic fractions were dried (Na2SO4)
14. customthe solvent was evaporated under reduced pressure