反应详情

To a solution of aluminum chloride (35.0 g, 262.5 mmol) in dichloromethane (75 mL) was added a solution of (2-Methoxy-phenyl)-acetic acid methyl ester (13.5 g, 75.0 mmol) and acetyl chloride (5.86 mL, 82.5 mmol)in dichloromethane (75 mL) dropwise. After the addition was complete the reaction was heated to reflux for 5 hours. The reaction mixture was then cooled and carefully poured onto a mixture of ice and water. The aqueous layer was then extracted with ethyl acetate (2×400 mL). The combined extracts were then washed with saturated sodium chloride (1×100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a solid. 1H NMR (400 MHz, DMSO): δ 10.51 (s, 1H), 7.79 (m, 2H), 6.88 (d, 1H), 3.63 (s, 2H), 3.59 (s, 3H), 2.47 (s, 3H). Mass Spectrum (Chemical Ionization, 1% NH3 in CH4) m/z 209 (M+H).

1. additionAfter the addition
2. temperaturewas heated
3. temperatureto reflux for 5 hours
4. temperatureThe reaction mixture was then cooled
5. extractionThe aqueous layer was then extracted with ethyl acetate (2×400 mL)
6. washThe combined extracts were then washed with saturated sodium chloride (1×100 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto yield a solid