反应详情

A solution of 3-hydroxy-4-methyl-benzoic acid methyl ester (7.7 g, 32.43 mmol), potassium carbonate (6.72 g, 48.65 mmol) and 1-iodo-3-methoxy propane (7.14 g, 35.68 mmol) in acetonitrile (125 mL) is stirred at reflux for 26 h. The solvent is concentrated under reduced pressure, H2O (100 mL) is added, and the aqueous layer is extracted with ether (50 mL×4). The combined organic extracts are washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title which is used without further purification in the next step. TLC, Rf (hexane/AcOEt 2:1)=0.65. 1H-NMR (CDCl3, 300 MHz): δ=2.10 (p, 2H), 2.3 (s, 3H), 3.38 (s, 3H), 3.62 (t, 2H), 3.9 (s, 3H), 4.15 (t, 2H), 7.15 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H) ppm.

1. temperatureat reflux for 26 h
2. concentrationThe solvent is concentrated under reduced pressure, H2O (100 mL)
3. additionis added
4. extractionthe aqueous layer is extracted with ether (50 mL×4)
5. washThe combined organic extracts are washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customto afford the title which
9. customis used without further purification in the next step