Phenol → N-Methyl-N-(3-phenoxypropyl)benzenamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 23a (0.20 g, 0.88 mmol) and phenol (0.75 g, 0.79 mmol) in DMF (5.0 mL) was added K2CO3 (0.24 g, 1.75 mmol). The reaction was then stirred at 80° C. for 12 hours. The reaction mixture was concentrated and purified by column chromatography to isolate the compound 23 as a colorless oil (0.12 g, 0.49 mmol, 56.7% yield). MS (ESI, positive) m/z calcd. for C16H20NO [M+H]+: 242.15, found: 241.93. 1H NMR (CDCl3, 400 MHz) δ7.22-7.33 (m, 4H), 6.92-6.99 (m, 3H), 6.69-6.77 (m, 3H), 4.04 (t, J=6.0 Hz, 2H), 3.58 (t, J=6.8 Hz, 2H), 2.97 (s, 3H), 2.06-2.12 (m, 2H).

Provenance & Evidence