Nitrogen → 1-(4-(3-Hydroxypropoxy)-3,5-dimethoxyphenyl)ethanone

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1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone (3.0 g, 15.3 mmol), 18-crown-6 (0.0606 g, 0.229 mmol) and potassium carbonate (2.74 g, 19.9 mmol) were taken in a two neck round bottom flask equipped with a stir bar. The flask was vacuumed and refilled with N2 three times. Acetone (30 mL) was added through syringe and needle. The mixture was stirred at room temperature for 30 minutes, followed by addition of 1-bromo-3-propanol (1.6 mL, 18.3 mmol). The mixture was refluxed for 24 hours and then filtered. Acetone was removed under vacuum to yield the crude product (3.8 g) which was used in the next step without purification. Purification can be performed by column chromatography (30% ethyl acetate and 70% hexane) to get pure product (1.64 g): 1H NMR (300 MHz, DMSO-d6) δ ppm 1.76 (t, J=6.44 Hz, 2H) 2.55 (s, 3H) 3.54 (d, J=5.27 Hz, 2 H) 3.82 (s, 6 H) 4.01 (q, J=7.03 Hz, 2 H) 7.22 (s, 2 H).

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