I. M. Pastor, M. Yus / Tetrahedron 57 (2001) 2365±2370
2369
4.2.7. 1-(2-Hydroxymethylphenyl)-4-phenyl-2-butanol
(2bc). Rf 0.31 (hexane/ethyl acetate:2:1); n (®lm) 3583±
3120 (OH), 3060, 3024, 1494, 1453 (CvCH), 1015 cm21
(C±O); dH 1.90 (2H, m, CHCH2CH2), 2.64±2.86 (4H, m,
CH2CHCH2CH2), 3.52 (2H, brs, 2£OH), 3.77 (1H, m, CH),
4.43 (1H, d, J11.8 Hz, HOCHH), 4.69 (1H, d, J11.8 Hz,
HOCHH), 7.15±7.31 (9H, m, ArH); dC 32.1, 39.3, 39.8
(3£CH2), 63.2 (CH2OH), 72.3 (CH), 125.9, 126.7, 128.4,
128.5, 130.0, 130.4, 137.9, 139.3, 141.8 (12C, ArC); m/z
238 (M1218, 1%), 116 (10), 105 (17), 104 (100), 91 (36),
91 (36), 77 (11); HRMS: M12 [H2O], found 238.1365.
C17H18O requires 238.1358.
(11), 65 (41), 63 (21), 53 (15), 52 (13), 51 (45), 50 (16), 44
(18), 40 (23).
4.2.12. 1-(3-Hydroxyphenyl)-1-phenyl-1-ethanol (2cb).10
Rf 0.38 (hexane/ethyl acetate: 2:1); n (®lm) 3583±3150
(OH), 3062, 3042, 1492, 1447 (CvCH), 1267, 1235,
1067 cm21 (C±O); dH 1.85 (3H, s, CH3), 2.79 (2H, brs,
2£OH), 6.40, 6.67, 6.81, 6.91, 7.17±7.28, 7.33 (1H, 1H,
1H, 1H, 2H and 2H, respectively, 6m, ArH), 7.09 (1H, t,
J7.9 Hz, ArH); dC 30.5 (CH3), 76.5 (C), 113.1, 114.1,
118.2, 125.8, 127.0, 128.1, 129.3, 147.4, 149.5, 155.6
(12C, ArC); m/z 214 (M1, 7%), 199 (29), 196 (17), 121
(19), 105 (37), 77 (22), 65 (11), 51 (16), 43 (100).
4.2.8. 2-(2-Hydroxymethylphenyl)-1-(2-methoxyphenyl)-
1-ethanol (2bd). Rf 0.30 (hexane/ethyl acetate: 2:1); n
(®lm) 3382±3079 (OH), 3033, 3011, 1493, 1464
(CvCH), 1059, 1007 cm21 (C±O); dH 3.01±3.16 (2H, m,
CH2CH), 3.65 (2H, s, 2£OH), 3.89 (3H, s, OCH3), 4.50 (1H,
d, J11.8 Hz, CHHOH), 4.80 (1H, d, J11.8 Hz,
CHHOH), 5.18 (1H, dd, J8.9, 3.6 Hz, CHOH), 6.93 (1H,
d, J8.5 Hz, ArH), 6.99 (1H, t, J7.5 Hz, ArH), 7.14±7.35
(5H, m, ArH), 7.43 (1H, dd, J7.5, 1.6 Hz, ArH); dC 39.9
(CH2), 55.3 (CH3), 63.3 (CH2OH), 70.9 (CH), 110.3, 120.8,
126.1, 126.8, 128.3, 128.5, 129.9, 130.6, 132.2, 138.0,
139.6, 156.0 (ArC); m/z 240 (M1218, 8%), 137 (25), 121
(12), 107 (145), 105 (11), 104 (100), 103 (10), 91 (13), 78
(14), 77 (19), 51 (11); HRMS: M1, found 258.1256.
C16H18O3 requires 258.1256.
4.2.13. 4-Hydroxyphenyl-phenylmethanol (2da). Rf 0.27
(hexane/ethyl acetate: 2:1); n (®lm) 3483±3170 (OH),
3063, 3037, 1513, 1448 (CvCH), 1234, 1005 cm21 (C±
O); dH (CD3OD) 2.37 (2H, brs, 2£OH), 5.76 (1H, s, CH),
6.77, 7.11±7.38 (2H and 7H, respectively, 2m, ArH); dC
(CD3OD) 75.2 (CH), 114.8, 126.1, 126.7, 127.8, 127.9,
135.1, 144.1, 155.8 (12C, ArC); m/z 200 (M1, 25%), 199
(11), 183 (15), 182 (56), 181 (19), 154 (20), 153 (76), 152
(38), 151 (10), 128 (14), 123 (30), 122 (20), 121 (74), 96
(13), 94 (66), 93 (10), 79 (20), 78 (22), 77 (100), 76 (56), 75
(12), 74 (12), 66 (10), 65 (32), 64 (33), 63 (36), 62 (12), 55
(11), 53 (12), 52 (15), 51 (80), 50 (36); HRMS: M1, found
200.0844. C13H12O2 requires 200.0837.
4.2.14. 1-(4-Hydroxyphenyl)-1-phenyl-1-ethanol (2db).10
Rf 0.35 (hexane/ethyl acetate: 2:1); n (®lm) 3583±3130
(OH), 3060, 3044, 1490, 1445 (CvCH), 1265, 1230,
1052 cm21 (C±O); dH 1.63 (3H, s, CH3), 3.70 (2H, brs,
2£OH), 6.80, 7.13±7.49 (1H and 8H, respectively, 2m,
ArH); dC 32.7 (CH3), 77.2 (C), 114.9, 125.4, 125.7, 126.6,
128.3, 128.8, 129.6, 138.4, 155.4 (12C, ArC); m/z 202
(M1214, 25%), 154 (18), 153 (10), 142 (15), 141 (100),
115 (28).
4.2.9. 1-(2-Hydroxymethylphenyl)-2-heptanol (2bh).8 Rf
0.36 (hexane/ethyl acetate:2:1); n (®lm) 3575±3103 (OH),
3064, 3020, 1455 (CvCH), 1019 cm21 (C±O); dH 0.91
(3H, deformed t, J6.7 Hz, CH3), 1.29±1.59 (10H, m,
(CH2)4 and 2£OH), 2.79 (2H, m, CH2CH), 3.73 (1H, m,
CH), 4.42 (1H, d, J11.8 Hz, CHHOH), 4.70 (1H,d,
J11.8 Hz, CHHOH), 7.20, 7.27 (2H and 2H, respectively,
2m, ArH); dC 14.0 (CH3), 22.6, 25.4, 31.8, 37.8, 39.7
(5£CH2), 63.1 (CH2OH), 73.1 (CH), 126.6, 128.3, 129.9,
130.3, 138.1, 139.4 (ArC); m/z 204 (M1218, 7%), 105
(17), 104 (100), 91 (10), 77 (10), 55 (11), 43 (11), 41 (14).
Acknowledgements
The work was ®nancially supported by the D.G.E.S. (no.
Â
Cultura (M.E.C.) and Generalitat Valenciana (no.
GVDOC99-2-4). I. M. P. thanks the Generalitat Valenciana
for a fellowship.
4.2.10. 6-(2-Hydroxymethylbenzyl)-6-undecanol (2bi). Rf
0.55 (hexane/ethyl acetate: 2:1); n (®lm) 3545±3114 (OH),
3063, 3018, 1459 (CvCH), 1018 cm21 (C±O); dH 0.91
(6H, deformed t, J6.8 Hz, 2£CH3), 1.26±1.54 (16H, m,
2£(CH2)4), 2.87 (2H, s, CH2COH), 4.57 (2H, s, CH2COH),
7.17, 7.11±7.29, 7.34 (1H, 2H and 1H, respectively, 3m,
ArH); dC 14.1 (2C, 2£CH3), 22.6, 23.4, 32.3, 39.0,
41.3 (9C, 2x(CH2)4 and ArCH2C), 63.3 (CH2OH), 74.5
(COH), 126.8, 127.6, 130.6, 131.9, 136.0, 140.5 (ArC);
m/z 256 (M1236, 0.5%), 203 (16), 105 (21), 104
(100), 71 (11), 55 (23), 43 (53), 41 (28); HRMS: M12
[H2O]2 [(CH2)4CH3], found 203.1432. C14H19O requires
203.1436.
PB97-0133) from the Spanish Ministerio de Educacion y
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4.2.11. 3-(Hydroxyphenyl)phenylmethanol (2ca).9 Rf 0.31
(hexane/ethyl acetate: 2:1); n (®lm) 3490±3238 (OH),
3087, 3025, 1451 (CvCH), 1255, 1037 cm21 (C±O); dH
2.88 (2H, brs, 2£OH), 5.78 (1H, s, CH), 7.11±7.39 (9H,
m, ArH); dC 79.1 (CH), 118.9, 126.5, 126.9, 127.1, 127.6,
127.9, 128.1, 128.2, 128.5, 129.7, 144.3, 152.1 (ArC); m/z
200 (M1, 33%), 181 (16), 153 (12), 152 (10), 105 (99), 95
(72), 94 (64), 93 (18), 91 (13), 79 (36), 78 (21), 77 (100), 66
È
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