4-(PHENOXYMETHYL)ANILINE synthesis

Yield:57181-90-5 95%

Reaction Conditions:

with hydrogen in methanol at 20; under 760.051 Torr; for 1.5 h;chemoselective reaction;

Steps:

Typical procedure for hydrogenation of 4-methylphenyl 4-nitrobenzyl ether (2a) to 4-methylphenyl 4-aminobenzyl ether (1a)

General procedure: A mixture of 2a (243mg, 1mmol) and 1% Pd/Ni bimetallic catalyst (73mg, 30wt%) in MeOH (10mL) was stirred under H₂ at room temperature and atmospheric pressure (on an atmospheric pressure hydrogenation apparatus) until the absorption of hydrogen ceased (90 min). After the catalyst was removed off by a magnetic stirring bar, the solution was evaporated on a rotavapor to give the product 1a as yellowish oil (210mg, 98%), which is pure enough for ¹H and ¹³C NMR determinations. IR (KBr) v 3372, 1623, 1519, 1233cm^-1; ¹H NMR (CDCl₃, 400MHz) δ 7.26-7.20 (m, 2H), 7.06 (d, 2H, J=11.0Hz), 6.87 (d, 2H, J=11.0Hz), 6.69 (d, 2H, J=11.0Hz), 4.90 (s, 2H), 3.69 (s, 2H), 2.28 (s, 3H); ¹³C NMR (CDCl₃, 100MHz) 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): calcd for C₁₄H₁₅NO, [M+Na]⁺: 236.1046, found: 236.1044.

References:

Chen, Wenwen;Bao, Hailin;Wang, Dingsheng;Wang, Xinyan;Li, Yadong;Hu, Yuefei [Tetrahedron,2015,vol. 71,# 49,p. 9240 - 9244]