Nitrogen → HCID 43090068, compound

Participants

Reaction Steps

4-hydroxyacetophenone (10.0 g, 73.5 mmol), 18-crown-6 (0.2912 g, 1.1 mmol) and potassium carbonate (13.2 g, 95.5 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 (22 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 (7.8 mL, 88.1 mmol). The mixture was refluxed for 24 hours and then filtered. Acetone was removed under vacuum to yield the crude product (15.0 g) which was used in the next step without purification. Purification can be performed by column chromatography (30% ethyl acetate and 70% hexane): mp 37-41° C.; 1H NMR (500 MHz, DMSO-d6) δ 1.86-1.91 (m, 2H), 2.50 (s, 3H, overlap with DMSO), 3.56 (m, 2H), 4.13 (t, J=6.36 Hz, 2H), 4.55 (t, J=5.14 Hz, 1H), 7.03 (d, J=8.80 Hz, 2H), 7.92 (d, J=9.05 Hz, 2H); 13C NMR (125 MHz, DMSO-d6) δ 26.3 (s), 31.9 (s), 57.1 (s), 64.9(s), 114.1(s), 129.7 (s), 130.3 (d), 162.5 (s), 196.1 (s); IR (ATR) ν 3439, 2941, 1654, 1595, 1255, 1170, 1056, 948, 827 cm-1; MS (ESI) m/z calc for C11H14NaO3 [MNa]+ 217.1, found 216.8. NMR results were consistent with the previously reported characterization in CDCl3.4

Provenance & Evidence