M-Cresol → 3-(methoxymethoxy)toluene

Participants

Reaction Steps

To m-cresol (19.4 mL, 188 mmol) in DMF (1 L) was added NaH (60% disp. in oil, 9.04 g, 0.226 mmol) in several portions. The mixture was stirred at rt for 30 min, chloromethyl methyl ether (11.5 mL, 151 mmol) was added in one portion, and the reaction mixture was stirred at room temperature overnight, partitioned between 1N aq. NaOH and Et2O. The organic phase was washed with 1N aq. NaOH, dried over MgSO4, filtered and concentrated in vacuo, to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.18 (t, 1H), 6.86-6.77 (m, 3H), 5.18 (s, 2H), 3.43 (s, 3H), 2.29 (s, 3H).

Provenance & Evidence