SYNTHESIS OF HOMOALLYL ALCOHOLS
1669
1-(2-Methoxylphenyl)-3-butenyl alcohol (1c). A colorless viscous liquid
with yield of 94%. 1H NMR (400 MHz, CDCl3) (d, ppm): 7.35–7.22 (m, 2H,
Ar-H), 6.98–6.86 (m, 2H, Ar-H), 5.90–5.80 (m, 1H, ¼CH), 5.16–5.08 (m, 2H,
¼CH2), 4.98–4.93 (m, 1H, CH), 3.84 (s, 3H, CH3), 2.62–2.46 (m, 3H, CH2 & OH);
13C NMR (100 MHz, CDCl3) (d, ppm): 156.2, 135.1, 131.7, 128.2, 126.7, 120.6,
117.4, 110.3 (all unsaturated CH2 and CH), 69.4 (C-O), 55.1 (CH3), 41.8 (CH2).
1-(3-Methoxylphenyl)-3-butenyl alcohol (1d). A colorless viscous liquid.
1H NMR (400 MHz, CDCl3): (d, ppm): 7.25 (d, J ¼ 8.0 Hz, 1H, Ar-H), 6.93–6.91
(m, 2H, Ar-H), 6.82–6.79 (m, 1H, Ar-H), 5.80 (dd, J ¼ 4.0 Hz, J ¼ 16.8 Hz, 1H,
¼CH), 5.18–5.12 (m, 2H, ¼CH2), 4.71–4.68 (m, 1H, -CH), 3.80 (s, 3H, CH3),
2.51–2.47 (m, 2H, -CH2), 2.15 (s, 1H, OH); 13C NMR (100 MHz, CDCl3) (d,
ppm): 159.8, 145.6, 134.4, 129.4, 118.3, 118.1, 112.9, 112.3 (all unsaturated CH2
and CH), 73.2 (C-O), 55.2 (CH3), 43.7 (CH2).
1-(4-Methoxylphenyl)-3-butenyl alcohol (1e). A colorless viscous liquid.
1H NMR (400 MHz, CDCl3) (d, ppm): 7.27–7.24 (m, 2H, Ar-H), 6.88–6.85 (m,
2H, Ar-H), 5.83–5.72 (m, 1H, ¼CH), 5.16–5.09 (m, 2H, ¼CH2), 4.67–4.63 (m, 1H,
-CH), 3.80 (s, 3H, CH3), 2.49–2.45 (m, 2H, CH2), 2.35 (s, 1H, OH); 13C NMR
(100 MHz, CDCl3) (d, ppm): 158.8, 136.0, 134.6, 127.0, 118.0, 113.6 (all unsaturated
CH2 and CH), 72.9 (C-O), 55.4 (CH3), 43.6 (CH2).
1-(2-Chlorophenyl)-3-butenyl alcohol (1f). A colorless viscous liquid.
1H NMR (400 MHz, CDCl3) (d, ppm): 7.57–7.54 (m, 1H, Ar-H), 7.33–7.23 (m,
2H, Ar-H), 7.21–7.17 (m, 1H, Ar-H), 5.91–5.81 (m, 1H, ¼CH), 5.20–5.13 (m, 3H,
CH & ¼ CH2), 2.65–2.59 (m, 1H, OH), 2.41–2.20 (m, 2H, CH2); 13C NMR
(100 MHz, CDCl3) (d, ppm): 141.1, 134.2, 131.6, 129.3, 128.4, 127.1, 127.0, 118.7
(all unsaturated CH2 and CH), 69.5 (C-O), 42.0 (CH2).
1-(4-Chlorophenyl)-3-butenyl alcohol (1g). A colorless viscous liquid.
1H NMR (400 MHz, CDCl3) (d, ppm): 7.32–7.23 (m, 4H, Ar-H), 5.80–5.74 (m,
1H, ¼CH), 5.17–5.13 (m, 2H, ¼CH2), 4.72–4.48 (m, 1H, CH), 2.49–2.42 (m, 2H,
CH2), 2.19–2.16 (m, 1H, OH); 13C NMR (100 MHz, CDCl3) (d, ppm): 142.2,
133.9, 133.1, 128.5, 127.2, 118.8 (all unsaturated CH2 and CH), 72.5 (C-O), 43.8
(CH2).
1-(2,4-Dichlorophenyl)-3-butenyl alcohol (1h). A white crystal, mp:
1
59–60 ꢀC. H NMR (400 MHz, CDCl3) (d, ppm): 7.51–7.48 (m, 1H, Ar-H), 7.34
(dd, J ¼ 2.0 Hz, J ¼ 3.6 Hz, 1H, Ar-H), 7.28–7.25 (m, 1H, Ar-H), 5.89–5.79 (m,
1H, ¼CH), 5.20–5.16 (m, 2H, ¼CH2), 5.12–5.08 (m, 1H, -CH), 2.63–2.57 (m, 1H,
OH), 2.39–2.25 (m, 2H, CH2); 13C NMR (100 MHz, CDCl3) (d, ppm): 139.8,
133.8, 133.4, 132.2, 129.1, 128.1, 127.3, 119.1 (all unsaturated CH2 and CH), 69.1
(C-O), 42.0 (CH2).
1-(4-Bromophenyl)-3-butenyl alcohol (1i). A colorless viscous liquid.
1H NMR (400 MHz, CDCl3) (d, ppm): 7.45 (dd, J ¼ 6.4 Hz, J ¼ 8.4 Hz, 2H, Ar-H),
7.22–7.19 (m, 2H, Ar-H), 5.79–5.72 (m, 1H, ¼CH), 5.17–5.12 (m, 2H, ¼CH2),
4.69–4.65 (m, 1H, -CH), 2.48–2.41 (m, 2H, CH2), 2.87–2.80 (m, 1H, OH); 13C
NMR (100 MHz, CDCl3) (d, ppm): 142.8, 133.9, 131.4, 127.6, 121.2, 118.8 (all
unsaturated CH2 and CH), 72.6 (C-O), 43.8 (CH2).