Synthesis
General procedure for the synthesis of 4-methoxymethylaniline from 1-(methoxymethyl)-4-nitrobenzene: a mixture of 1-(methoxymethyl)-4-nitrobenzene (243 mg, 1 mmol) with 1% Pd/Ni bimetallic catalyst (73 mg, 30 wt%) in methanol (10 mL) was placed in an atmospheric pressure hydrogenation unit and stirred at room temperature and atmospheric pressure until hydrogen absorption ceased (about 90 min). Upon completion of the reaction, the catalyst was removed by means of a magnetic stirring bar and the solution was subsequently evaporated using a rotary evaporator to afford the target product, 4-methoxymethylaniline (1a), as a yellow oil (210 mg, 98% yield), which was sufficiently pure to be analyzed by 1H and 13C NMR. νmax by IR (KBr): 3372, 1623, 1519, 1233 cm1; 1H NMR (CDCl3, 400 MHz) δ: 7.26-7.20 (m, 2H), 7.06 (d, 2H, J = 11.0 Hz), 6.87 (d, 2H, J = 11.0 Hz), 6.69 (d, 2H, J = 11.0 Hz), 4.90 (s, 2H), 3.69 (s, 2H) 2.28 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ: 156.8, 146.3, 129.7 (2C), 126.8, 115.0 (2C), 114.6 (2C), 70.1, 20.4. HRMS (ESI-TOF) m/z: [M + Na]+ calcd for C14H15NO, 236.1046; found, 236.1044.
References
[1] Tetrahedron, 2015, vol. 71, # 49, p. 9240 - 9244
[2] Synlett, 1998, # 9, p. 1028 - 1028
[3] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 9, p. 955 - 977
[4] Chemistry - A European Journal, 2007, vol. 13, # 4, p. 1291 - 1299
[5] Journal of the Chemical Society, 1954, p. 4127,4132
