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ChemicalBook CAS DataBase List 2-(PHENOXYMETHYL)ANILINE
78584-41-5

2-(PHENOXYMETHYL)ANILINE synthesis

6synthesis methods
-

Yield:78584-41-5 97%

Reaction Conditions:

with hydrogen in methanol at 20; under 760.051 Torr; for 1.66667 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]

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