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27
CH2CO, OH), 1.86 and 1.52 (3 and 3H, respectively, 2s,
2ꢅMe); dC (75 MHz, CDCl3) 148.0, 147.45, 142.0 (2C),
128.1 (4C), 128.0, 126.7 (2C), 126.5, 125.7 (2C), 125.65,
1511, 1493, 1058, 1035, 1024, 1016 cmꢁ1; dH (300 MHz,
CDCl3) 7.30ꢂ7.20 and 7.10ꢂ7.05 (13 and 1H, respec-
tively, 2m, ArH), 5.72 (1H, s, CCHOC), 4.60ꢂ4.55 (1H,
m, CCHOCH2), 2.70ꢂ1.19 (6H, m, CH2CH2, 2ꢅOH);
/
/
/
/
124.65 (2C), 123.35, 76.05, 74.55, 45.7, 30.7, 30.45,
30.25; m/z (EI) 328 (3, [Mꢃꢁ
/
/
/18]), 310 (37), 217 (10),
dC (75 MHz, CDCl3) 144.4, 143.85, 141.35, 141.05,
128.45 (2C), 128.4 (2C), 128.35 (2C), 127.55, 127.35,
126.6 (2C), 126.4 (2C), 125.85 (2C), 75.9, 73.7, 40.25,
208 (27), 207 (29), 206 (32), 205 (11), 193 (57), 192 (11),
191 (23), 179 (18), 178 (56), 165 (11), 130 (20), 129 (18),
121 (62), 115 (24), 103 (43), 91 (49), 77 (25), 51 (14), 43
(100); HRMS (EI) [Mꢃ], Found: 346.1945. C24H26O2
requires 346.1933%.
31.6; m/z (EI) 318 (B
1, [Mꢃ]), 196 (11), 195 (15), 194
/
(72), 193 (40), 181 (17), 180 (100), 179 (15), 178 (16), 165
(15), 117 (12), 115 (14), 107 (80), 106 (11), 105 (80), 92
(12), 91 (36), 79 (46), 77 (51), 51 (10)); Anal. Found: C,
82.85; H, 6.91. Calc. for C22H22O2: C, 82.99; H, 6.96%.
4.3.1.9. 1-{2-[3-(1-Hydroxycyclohexyl)phenyl]ethyl}-
1-cyclohexanol (2h). Yield 63%; m.p. 84ꢂ
acetateꢂhexane); Rf (hexaneꢂethyl acetate: 1/2) 0.71;
nmax (melted film) 3415, 3023, 1604, 1169, 1133 cmꢁ1
dH (300 MHz, CDCl3) 7.35, 7.30ꢂ7.20 and 7.05ꢂ7.00 (1,
2 and 1H, respectively, s, m and m, respectively, ArH),
2.70ꢂ2.65 (2H, m, CH2Ar), 1.98 (2H, s, 2ꢅOH), 1.70ꢂ
1.25 (22H, m, 2ꢅ(CH2)5 and ArCH2CH2); dC (75 MHz,
/
86 8C (ethyl
/
/
4.3.1.12. 4-[4-(1-Hydroxy-1-methylethyl)phenyl]-2-
;
methyl-2-butanol (2k). Yield 60%; Rf (hexaneꢂethyl
/
/
/
acetate: 1/1) 0.37; nmax (liquid film) 3371, 3088, 3052,
3023, 1613, 1510, 1212, 1169, 1146 cmꢁ1; dH (300 MHz,
/
/
/
CDCl3) 7.38 and 7.15 (2 and 2H, respectively, 2d, Jꢄ
8.5 Hz, ArH), 2.70ꢂ2.65 (2H, m, CH2CH2CO), 2.18
(2H, s, 2ꢅOH), 1.80ꢂ1.75 (2H, m, CH2CO), 1.55 and
1.26 (6 and 6H, respectively, 2s, 4ꢅMe); dC (75 MHz,
/
/
/
CDCl3) 149.55, 142.55, 128.0, 126.5, 124.55, 121.85,
72.95, 71.3, 44.2, 38.65 (2C), 37.3 (2C), 29.45, 25.7, 25.4,
/
/
/
22.15 (2C), 22.0 (2C); m/z (EI) 284 (20, [Mꢃꢁ
18]), 267
/
CDCl3) 146.55, 140.7, 127.95 (2C), 124.4 (2C), 72.2,
70.75, 45.55, 31.6 (2C), 30.1, 29.15 (2C); m/z (EI) 222
(16), 266 (83), 223 (11), 190 (15), 186 (14), 185 (19), 184
(47), 183 (18), 173 (15), 172 (68), 171 (100), 170 (19), 169
(12), 158 (11), 157 (22), 155 (15), 145 (18), 144 (12), 143
(34), 142 (20), 141 (35), 131 (12), 130 (26), 129 (59), 128
(47), 127 (12), 118 (12), 117 (29), 115 (32), 105 (27), 104
(22), 99 (27), 95 (37), 93 (13), 91 (45), 81 (62), 80 (24), 79
(41), 77 (28), 67 (39), 65 (13), 55 (77), 53 (29), 43 (33), 41
(85); Anal. Found: C, 79.38; H, 10.08. Calc. for
C20H30O2: C, 79.42; H, 10.00%.
(B
1, [Mꢃ]), 204 (13), 189 (33), 186 (32), 171 (19), 143
/
(22), 133 (11), 131 (74), 129 (18), 128 (11), 115 (15), 105
(10), 91 (21), 59 (41), 43 (100), 41 (15); HRMS (EI)
[Mꢃ], Found: 222.1615. C14H22O2 requires 222.1620%.
4.3.1.13. 3-Ethyl-1-[4-(1-ethyl-1-
hydroxypropyl)phenyl]-3-pentanol (2l). Yield 85%; Rf
(hexaneꢂ
3089, 3051, 3022, 1614, 1511, 1159 cmꢁ1; dH (300 MHz,
CDCl3) 7.3 and 7.16 (2 and 2H, respectively, 2d, Jꢄ7.9
Hz, ArH), 2.65ꢂ2.60 (2H, m, CH2CH2CO), 1.85ꢂ1.70
and 1.54 (7 and 5H, respectively, 2m, 5ꢅCH2CO, 2ꢅ
OH), 0.90 and 0.75 (6 and 6H, respectively, 2t, Jꢄ7.3
Hz, 4ꢅMe); dC (75 MHz, CDCl3) 143.15, 140.5, 127.8
(2C), 125.45 (2C), 77.2, 74.55, 40.1, 34.7 (2C), 30.9 (2C),
29.3, 7.8 (2C), 7.75 (2C); m/z (EI) 260 (B 18]),
1, [Mꢃꢁ
/
ethyl acetate: 7/3) 0.54; nmax (liquid film) 3439,
4.3.1.10. 1-[4-(1-Hydroxy-2,2-dimethylpropyl)phenyl]-
/
4,4-dimethyl-3-pentanol (2i). Yield 78%; m.p. 112ꢂ
114 8C (ethyl acetateꢂhexane); Rf (hexaneꢂethyl ace-
tate: 7/3) 0.47; nmax (melted film) 3439, 3088, 3048, 1614,
1511, 1048, 1009 cmꢁ1; dH (300 MHz, CDCl3) 7.20ꢂ
7.15 (4H, m, ArH), 4.34 (1H, s, CCHOC), 3.20ꢂ3.15,
2.95ꢂ2.85 and 2.65ꢂ2.55 (1, 1 and 1H, respectively, 3m,
CH2CH2CHO), 1.90ꢂ1.75 and 1.60ꢂ1.55 (3 and 1H,
respectively, 2m, CH2CO, 2ꢅOH) 0.91 and 0.87 (9 and
9H, respectively, 2s, 6ꢅMe); dC (75 MHz, CDCl3)
141.35, 139.65, 127.6 (4C), 82.15, 79.3, 35.55, 34.9,
33.35, 32.95, 25.9 (3C), 25.6 (3C); m/z (EI) 278 (B1,
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
242 (18), 160 (13), 159 (100), 129 (13), 57 (17), 41 (21);
HRMS (EI) [Mꢃ], Found: 278.2210. C18H30O2 requires
278.2246%.
/
/
/
[Mꢃ]), 260 (15), 222 (10), 221 (73), 203 (18), 185 (12),
172 (52), 160 (17), 159 (100), 158 (11), 157 (26), 147 (22),
145 (18), 143 (23), 133 (56), 131 (13), 129 (27), 128 (15),
120 (27), 119 (73), 117 (48), 114 (16), 105 (86), 92 (11), 91
(91), 77 (11), 71 (22), 69 (40), 57 (77), 55 (15), 43 (28), 41
(81); Anal. Found: C, 77.61; H, 10.76. Calc. for
C18H30O2: C, 77.65; H, 10.86%.
4.3.1.14. 4-{[4-(1-Hydroxy-1-phenyl)ethyl]phenyl}-2-
phenyl-2-butanol (2m). Yield 54%; Rf (hexaneꢂethyl
/
acetate: 1/1) 0.61; nmax (liquid film) 3439, 3086, 3057,
3025, 1601, 1494, 1066 cmꢁ1; dH (300 MHz, CDCl3)
7.45ꢂ
ArH), 2.60ꢂ
(3H, m, CH2CO, OH), 1.87 and 1.55 (3 and 3H,
respectively, 2s, 2ꢅMe); dC (75 MHz, CDCl3) 148.05,
/
7.10 and 7.05ꢂ
/
7.00 (12 and 2H, respectively, 2m,
/
2.35 (3H, m, CH2CH2CO, OH), 2.20ꢂ
/2.00
/
4.3.1.11. 3-[4-Hydroxy(phenyl)methylphenyl]-1-phenyl-
147.45, 145.4, 140.8, 128.15 (2C), 127.95 (4C), 126.7,
126.55, 125.8 (2C), 125.7 (2C), 124.7 (2C), 75.95, 74.55,
1-propanol (2j). Yield 60%; m.p. 109ꢂ
acetateꢂhexane); Rf (hexaneꢂethyl acetate: 7/3) 0.18;
nmax (liquid film) 3543, 3369, 3085, 3060, 3028, 1602,
/
111 8C (ethyl
/
/
45.7, 30.7, 30.3, 29.85; m/z (EI) 328 (3, [Mꢃꢁ
(11), 310 (44), 208 (15), 207 (25), 206 (12), 194 (17), 193
/
18]), 311