Ammonia → 4-Ethoxy-2-methyl-1-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

3-Methyl-4-nitrophenol 403 (500 mg, 3.0 mmol) was dissolved in 2-butanone (10 mL). Potassium carbonate (903 mg, 6.5 mmol) was added to the solution followed by diethylsulfate (0.45 mL, 3.2 mmol). The reaction mixture was heated at 70° C. for 2 h. Upon completion, the mixture was cooled to rt and aqueous ammonia (30%, 1 mL) was added and stirred for 18 h at rt. The reaction mixture was filtered and washed with 2-butanone (30 mL). The filtrate was collected and evaporated in vacuo to yield a white solid (580 mg, 97%). mp 50-52° C. (lit.53 mp 51° C.). TLC Rf 0.65 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 8.11-8.09 (d, 1H, J=8.88 Hz), 6.82-6.78 (m, 2H), 4.14-4.10 (q, 2H, J=6.96 Hz), 2.65 (s, 3H), 1.48-1.46 (t, 3H, J=6.95 Hz). 13C NMR (150 MHz, CDCl3) δ 162.5, 142.0, 137.1, 127.6, 117.9, 112.2, 64.2, 21.8, 14.6.

Provenance & Evidence