1654
C. Zhou, Z. Wang
PAPER
13C NMR (CDCl3): d = 44.36, 55.44, 71.65, 110.54, 120.86, 126.45,
126.92, 128.43, 128.46, 129.65, 132.02, 139.08, 156.41.
1,2-Diphenylpropan-1-ol (4a)
FT-IR (KBr): 3424, 1602, 1494, 1073 cm–1.
GC-MS: m/z = 228.
1H NMR (CDCl3): d = 1.15 (anti) and 1.34 (syn) (d, J = 7.05 Hz, 3
H), 2.05–2.15 (br, 1 H), 3.06–3.11 (anti) and 3.12 (syn) (m, 1 H),
4.71 (anti) and 4.82 (syn) (d, J = 8.71, 5.90 Hz, 1 H), 7.32–7.45 (m,
10 H).
1-(2-Hydroxyphenyl)-2-phenylethanol (3j)
FT-IR (KBr): 3339, 1495, 1029 cm–1.
1H NMR (CDCl3): d = 2.68–2.90 (br, 1 H), 3.08 (d, 2 H, J = 6.98
Hz), 4.98 (t, 1 H, J = 6.98 Hz), 6.80–6.91 (m, 3 H), 7.16–7.33 (m, 5
H), 7.85–8.05 (br, 1 H).
13C NMR (CDCl3): d = 15.17, 18.46, 47.29, 48.20, 78.76, 79.75,
126.43, 126.52, 127.01, 127.11, 127.28, 127.91, 128.04, 128.15,
128.22, 128.31, 128.40, 128.77, 142.60, 142.61, 143.54, 143.55.
13C NMR (CDCl3): d = 44.92, 76.43, 117.09, 120.78, 127.43,
127.93, 129.77, 130.03, 130.41, 130.52, 138.31, 156.41.
MS: m/z = 214.
1-Piperonyl-2-phenylpropan-1-ol (4b)
GC-MS: m/z = 214.
FT-IR (KBr): 3418, 1603, 1039 cm–1.
1-(2-Hydroxy-5-methoxyphenyl)-2-phenylethanol (3k)
1H NMR (CDCl3): d = 1.03 (anti) and 1.28 (syn) (d, J = 7.13 Hz, 3
H), 2.08–2.12 (br, 1 H), 2.90–2.93 (anti) and 2.99–3.01 (syn) (m, 1
H), 4.52 (anti) and 4.62 (syn) (d, J = 9.41, 6.31 Hz, 1 H), 5.85 (syn)
and 5.88 (anti) (d, 2 H), 6.69–7.35 (m, 8 H).
13C NMR (CDCl3): d = 15.62, 18.54, 47.38, 48.24, 70.40, 70.41,
78.65, 79.57, 100.94, 101.08, 106.95, 107.18, 107.75, 107.97,
119.83, 120.75, 125.49, 126.49, 127.01, 127.52, 128.11, 128.15,
128.56, 128.80, 136.62, 137.17, 143.59, 143.64.
FT-IR (KBr): 3540, 1602, 1509, 1048 cm–1.
1H NMR (CDCl3): d = 3.11 (d, 2 H, J = 7.26 Hz), 3.15–3.25 (br, 1
H), 3.71 (s, 3 H), 4.94 (t, 1 H, J = 7.26 Hz), 6.47–6.49 (m, 1 H),
6.74–6.76 (m, 1 H), 6.80–7.82 (m, 1 H), 7.20–7.22 (m, 2 H) 7.29–
7.39 (m, 3 H), 7.74–7.76 (br, 1 H).
13C NMR (CDCl3): d = 44.08, 55.93, 71.36, 112.92, 114.18, 117.72,
126.92, 127.75, 128.68, 129.71, 137.65, 149.11, 152.89.
HRMS-GC: m/z calcd for C16H16O3, 256.1099; found, 256.1095.
HRMS-GC: m/z calcd for C15H16O3, 244.1099; found, 244.1097.
1-(2-Furanyl)-2-phenylpropan-1-ol (4d)
1,4-Diphenylbut-3-en-2-ol (3l)
FT-IR (KBr): 3419, 1602, 1495, 1070 cm–1.
FT-IR (KBr): 3388, 3026, 2921, 1601, 1494, 1071 cm–1.
1H NMR (CDCl3): d = 1.19 (anti) and 1.42 (syn) (d, J = 7.00 Hz, 3
H), 1.95–2.12 (br, 1 H), 3.29–3.34 (m, 1 H), 4.76 (anti) and 4.80
(syn) (d, J = 8.78, 6.50 Hz, 1 H), 6.09–6.40 (m, 3 H), 7.20–7.47 (m,
5 H).
13C NMR (CDCl3): d = 16.19, 18.35, 45.98, 45.66, 72.89, 73.00,
106.83, 107.80, 110.23, 110.32, 126.70, 127.18, 127.96, 128.09,
128.41, 128.87, 141.64, 142.23, 142.95, 143.33, 154.94, 155.60.
1H NMR (CDCl3): d = 1.90–2.12 (br, 1 H), 2.63–2.99 (m, 2 H),
4.49–4.52 (m, 1 H), 6.22–6.60 (m, 1 H), 6.55–6.60 (d, 1 H,
J = 15.88 Hz), 7.23–7.36 (m, 10 H).
13C NMR (CDCl3): d = 44.34, 73.62, 126.65, 126.78, 127.81,
128.70, 128.73, 129.75, 130.54, 131.64, 136.87, 137.84.
HRMS-GC (EI): m/z calcd for C16H16O, 224.1201; found,
224.1193.
HRMS–GC: m/z calcd for C13H14O2, 202.0994; found, 202.0988.
2-Phenylethanol (3m)
1-(4-Chlorophenyl)-2-phenylpropan-1-ol (4e)
FT-IR (KBr): 3355, 3027, 2940, 1604, 1496, 1045 cm–1.
FT-IR (KBr): 3418, 1600, 1491,1060 cm–1.
1H NMR (CDCl3): d = 2.74 (t, 2 H, J = 6.92 Hz), 3.22–3.30 (br, 1
H), 3.67 (t, 2 H, J = 6.92 Hz), 7.07–7.25 ( m, 5 H).
13C NMR (CDCl3): d = 38.77, 62.94, 125.91, 128.07, 128.67,
138.47.
1H NMR (CDCl3): d = 1.13 (anti) and 1.34 (syn) (d, J = 8.10 Hz, 3
H), 2.10–2.40 (br, 1 H), 2.99–3.01 (anti) and 3.07–3.09 (syn) (m, 1
H), 4.65 (anti) and 4.74 (syn) (d, J = 8.43, 6.00 Hz, 1 H), 7.12–7.41
(m, 9 H).
13C NMR (CDCl3): d = 15.23, 18.19, 47.32, 48.20, 78.16, 79.01,
126.71, 127.17, 127.84, 128.13, 128.20, 128.44, 128.47, 128.48,
128.50, 128.85, 132.30, 132.54, 133.43, 133.49, 135.44, 135.67,
141.07, 141.49, 142.99, 143.21.
HRMS-GC (EI): m/z = 122.
1-Phenyloctan-2-ol (3n)
FT-IR (KBr): 3383, 1574, 1495, 1080 cm–1.
1H NMR (CDCl3): m/z = 0.90 (t, 3 H, J = 6.64 Hz), 1.27–1.30 (m, 6
H), 1.52–1.54 (m, 4 H), 2.62–2.69 (m, 1 H), 2.70–2.81 (br, 1 H),
2.82–2.87 (m, 1 H), 3.78–3.86 (m, 1 H), 7.21–7.35 (m, 5 H).
13C NMR (CDCl3): d = 14.31, 22.83, 25.94, 29.53, 32.05, 37.05,
44.26, 72.92, 126.64, 128.76, 129.64, 138.86.
GC-HRMS: m/z calcd for C15H15OCl, 246.0811; found, 246.0810.
1-(4-Methoxyphenyl)-2-phenylpropan-1-ol (4g)
FT-IR (KBr): 3419, 1610, 1512, 1454,1035 cm–1.
1H NMR (CDCl3): d = 1.05 (anti) and 1.31 (syn) (d, J = 7.05 Hz, 3
H), 1.75–1.95 (br, 1 H), 2.99–3.01 (anti) and 3.06–3.08 (syn) (m, 1
H), 3.76 (syn) and 3.81 (anti) (s, 3 H), 4.61 (anti) and 4.74 (syn) (d,
J = 8.73, 6.03 Hz), 6.79–7.35 (m, 9 H).
13C NMR (CDCl3): d = 15.50, 18.53, 47.38, 48.33, 78.54, 79.39,
113.47, 113.80, 125.50, 126.48, 126.99, 127.59, 128.14, 128.23,
128.30, 128.62, 128.80, 134.82, 135.17, 143.73, 158.82, 159.33.
HRMS-GC: m/z calcd for C14H22O, 206.1671; found, 206.1671.
1-(4-Acetylphenyl)-2-phenylethanol (3o)
FT-IR (KBr): 3459, 2923, 1666, 1603, 1045 cm–1.
1H NMR (CDCl3): d = 2.21–2.38 (br, 1 H), 2.56 (s, 3 H), 2.99 (d, 2
H, J = 6.61 Hz), 4.93 (t, 1 H, J = 6.61 Hz), 7.14–7.17 (m, 2 H),
7.22–7.31 (m, 3 H), 7.40 (d, 2 H, J = 8.33 Hz), 7.89 (d, 2 H, J = 8.33
Hz).
HRMS–GC: m/z calcd for C16H18O2, 242.1307; found, 246.1310.
13C NMR (CDCl3): d = 26.67, 46.08, 74.86, 126.14, 126.87, 128.56,
128.65, 129.61, 136.43, 137.48, 149.27, 198.00.
1-(2-Chlorophenyl)-2-phenylpropan-1-ol (4h)
IR (KBr): 3440, 1600, 1575, 1493, 1060 cm–1.
1H NMR (CDCl3): d = 1.26 (syn) and 1.28 (anti) (d, J = 5.40 Hz, 3
H), 2.00–2.10 (br, 1 H), 3.13–3.17 (anti) and 3.35–3.40 (syn) (m, 1
HRMS-GC (CI): m/z calcd for C16H17O2 (M + H), 241.1229; found,
241.1244.
Synthesis 2005, No. 10, 1649–1655 © Thieme Stuttgart · New York