6-Chloro-2-[2-methoxy-3,5-bis(1,1-dimethylethyl)phenyl]-1-oxido-2H-benzotriazole (2h) white solid,
mp 186~189 oC. 1H NMR (300 MHz, CDCl3) δ 1.33 (s, 9H), 1.44 (s, 9H), 3.27 (s, 3H), 7.29 (s, 1H), 7.42
13
(d, 1H, J = 9.2 Hz), 7.61(s, 1H), 7.77 (d, 1H, J = 9.2 Hz), 7.85 (s, 1H); C NMR (75 MHz, CDCl3) δ
153.57, 146.14, 143.62, 140.13, 132.43, 130.80, 127.83, 126.30, 125.27, 123.78, 120.67, 113.28, 60.67,
35.67, 34.76, 31.19, 30.42; IR(CDCl3) 3107, 3084, 2972, 2901 cm-1; HRMS(EI) calcd for C21H26N3O2Cl
387.1714, found 387.1716. Anal. Calcd for C21H26N3O2Cl: C, 65.02; H, 6.76; N, 10.83. Found: C, 65.17;
H, 6.76; N, 10.85.
5-Chloro-2-[6-methoxy-3,5-bis(1,1-dimethylethyl)phenyl]-1-oxido-2H-benzotriazole (2i) white solid,
mp 135~137 oC. 1H NMR (300 MHz, CDCl3) δ 1.28 (s, 9H), 1.39 (s, 9H), 3.18 (s, 3H), 7.22-7.28 (m, 2H),
7.56 (d, 1H, J = 2.4 Hz), 7.73-7.76 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 153.69, 146.14, 143.59,
141.80, 135.01, 127.83, 127.72, 126.35, 123.81, 123.71, 118.18, 115.46, 60.69, 35.61, 34.74, 31.25,
30.46; IR (CDCl3) 3102, 2961, 2933, 2869 cm-1; HRMS(EI) calcd for C21H26N3O2Cl 387.1714, found
387.1708. Anal. Calcd for C21H26N3O2Cl: C, 65.02; H, 6.76; N, 10.83. Found: C, 65.17; H, 6.79; N, 10.79.
o
1
2-[2-Methoxy-5-methylphenyl]-1-oxido-2H-benzotriazole (2j) white solid, mp 93~95 C. H NMR
(500 MHz, CDCl3) δ 2.35 (s, 3H), 3.80 (s, 3H), 7.02 (d, 1H, J = 8.7 Hz), 7.29 (d, 1H, J = 1.8 Hz), 7.31-
7.44 (m, 3H), 7.75 (d, 1H, J = 8.7 Hz), 7.80 (d, 1H, J = 8.7 Hz); 13C NMR (125 MHz, CDCl3) δ 153.35,
141.67, 133.62, 130.57, 129.36, 128.72, 125.98, 125.37, 122.64, 119.26, 114.12, 112.46, 56.23, 20.21; IR
(CDCl3) 3074, 3017, 2964, 2934 cm-1; HRMS(EI) calcd for C14H13N3O2 255.1008, found 255.1007. Anal.
Calcd for C14H13N3O2: C, 65.87; H, 5.13; N, 16.46. Found: C, 65.43; H, 5.13; N, 16.46.
2-(2H-Benzotriazol-2-yl)-4,6-bis(1,1-dimethylethyl)phenol (3a) pale yellowish white solid, mp 153
~155 oC (lit.,5 mp 154~156 oC). 1H NMR (300 MHz, CDCl3) δ 1.39 (s, 9H), 1.51 (s, 9H), 7.40 (d, 1H, J =
2.0 Hz), 7.39-7.45 (m, 2H), 7.86-7.92 (m, 2H), 8.30 (d, 1H, J = 2 Hz), 11,76 (s, 1H); IR(CDCl3) 3500,
3060, 2950, 1435, 1395, 1150 cm-1; GC-MS m/z (rel. intensity) 323 (35, M+), 308 (100), 57 (5).
2-(2H-Benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)phenol (3b) white solid, mp 85~87 oC (lit.,5 mp
86.5~88 oC). 1H NMR (300 MHz, CDCl3) δ 0.66 (t, 3H, J = 7.5 Hz), 0.70 (t, 3H, J = 7.5 Hz), 1.36 (s, 6H),
1.45 (s, 6H), 1.68 (q, 2H, J = 7.5 Hz), 2.00 (q, 2H, J = 7.5 Hz), 7.28 (d, 1H, J = 2.0 Hz), 7.45 (m, 2H),
7.95 (m, 2H), 8.23 (d, 1H, J = 2.0 Hz), 11.74 (s, 1H); IR (CDCl3) 3400, 3055, 2950, 1453, 1373, 1251
cm-1; GC-MS m/z (rel. intensity) 351 (15, M+), 322 (100).
2-(5-Chloro-2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylethyl)phenol (3c) white solid, mp 151~153 oC
(lit.,5 mp 152.5~154.5 oC). 1H NMR (300 MHz, CDCl3) δ 1.39 (s, 9H), 1.50 (s, 9H), 7.45 (d, 1H, J = 2.0
Hz), 7.47 (d, 1H, J = 1.0 Hz), 7.85-7.95 (m, 2H), 8.36 (d, 1H, J = 2.0 Hz), 11.52 (s, 1H); IR(KBr disc)
3490, 3100, 2950, 1495, 1471, 1431, 1355, 1043 cm-1; GC-MS m/z (rel. intensity) 359 (5, M++2), 357 (15,
M+), 342 (100), 149 (60), 57 (8).