General procedure with Nafionꢀ
2-(Neopentyloxy)naphthalene 10. [1991-51-1]1H NMR
R
(300 MHz, CDCl3): 7.75 (m, 3H), 7.44 (m, 1H), 7.34 (m,
1H), 7.18 (m, 1H), 7.14 (s, 1H) 3.73 (s, 2H), 1.10 (s, 9H). 13C
NMR (CDCl3): 157.7, 134.8, 129.3, 128.9, 127.7, 126.8, 126.4,
123.5, 119.3, 106.6, 78.0, 32.0, 26.8. HRMS EI calculated for
[C15H18O]+ = 214.1352, found = 214.1353.
R
To dried Nafionꢀ NR50 (3.2 g), was added 2-naphthol
(25 mmol, 3.6 g) follow by 1-butanol (23 mL). The mixture
was stirred at 115 ◦C, during 35 h in a round bottom flask
under argon atmosphere. The reactional media was filtered and
concentrated. The crude was purified by column chromatog-
raphy (Cyclohexane–ethyl acetate 9/1) to afford 4.87 g of 2-
butoxynaphthalene (97%) as a yellow solid.
2-sec-Butoxynaphthalene 11. [90466-06-1] 1H NMR
(300 MHz, CDCl3): 7.74 (m, 3H), 7.43 (m, 1H), 7.33 (m, 1H),
7.15 (m, 2H), 4.47 (m, 1H), 1.77 (m, 2H), 1.38 (d, J = 6.0 Hz,
3H), 1.04 (t, J = 7.4 Hz, 3H); 13C NMR (CDCl3): 156.2, 134.8,
129.5, 128.9, 127.7, 126.8, 126.3, 123.6, 119.9, 108.5, 75.1, 29.3,
19.3, 9.9; HRMS EI calculated for [C14H16O]+ = 200.1196,
found = 200.1202.
2-Ethoxynaphthalene 1. [93-18-5] 1H NMR (300 MHz,
CDCl3): 7.74 (m, 3H), 7.41 (m, 1H), 7.33 (m, 1H), 7.14 (m,
2H), 4.14 (q, J = 6.6 Hz, 2H), 1.50 (t, J = 6.6 Hz, 3H); 13C NMR
(CDCl3): 157.0, 134.7, 129.4, 129.0, 127.7, 126.8, 126.4, 123.6,
119.1, 106.6, 63.4, 14.9; HRMS EI calculated for [C12H12O]+ =
172.0888, found = 172.0885.
1,6-Dibutoxynaphthalene 13. 1H NMR (300 MHz, CDCl3):
8.07 (d, 7.61, J = 8.2 Hz, 1H), 7.25 (m, 2H), 7.05 (m, 2H), 6.62
(m, 1H), 4.18 (m, 4H), 2.09 (m, 4H), 1.78 (m, 4H), 1.22 (m, 6
H). 13C NMR (CDCl3): 157.7, 155.2, 136.1, 126.7, 123.9, 120.9,
119.0, 117.9, 106.6, 102.8, 67.9, 67.8, 31.5, 31.4, 19.6, 19.5, 14.1,
14.0. HRMS EI calculated for [C18H24O2]+ = 272.1771, found =
272.1774.
2-Propoxynaphthalene 2. [19718-45-7] 1H NMR (300 MHz,
CDCl3): 7.76 (m, 3H), 7.45 (m, 1H), 7.34 (m, 1H), 7.17 (m, 2H),
4.06 (d, J = 6.6 Hz, 2H), 1.90 (m, 2H), 1.10 (t, J = 7.4 Hz,
3H); 13C NMR (CDCl3): 157.2, 134.7, 129.4, 129.0, 127.7, 126.8,
126.4, 123.6, 119.1, 106.7, 69.6, 22.7, 10.7; HRMS CI calculated
for [C13H14O+H]+ = 187,1123, found = 187.112.
7-Butoxynaphthalen-1-ol 14. 1H NMR (300 MHz, DMSO):
7.71 (d, J = 6.6 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H), 7.37 (d, J =
6.2 Hz, 1H), 7.16 (m, 2H), 6.69 (m, 1H), 4.11 (t, J = 4.2 Hz,
2H), 1.85 (m, 2H), 1.54 (m, 2 H), 1.00 (t, J = 5.5 Hz, 3H). 13C
NMR (CDCl3): 157.0, 150.5, 130.5, 129.3, 125.4, 123.3, 120.6,
119.7, 109.2, 100.7, 67.9, 31.4, 19.5, 14.0. HRMS EI calculated
for [C14H16O2]+ = 216.1145, found = 216.155.
1
2-Butoxynaphthalene 3. [10484-56-7] H NMR (300 MHz,
CDCl3): 7.76 (m, 3H), 7.44 (m, 1H), 7.33 (m, 1H), 7.16 (m, 2H),
4.09 (t, J = 6.5 Hz, 2H), 1.85 (m, 2H), 1.55 (m, 2H), 1.02 (t, J =
7.4 Hz, 3H); 13C NMR (CDCl3): 157.3, 134.8, 129.4, 129.0, 127.8,
126.8, 126.4, 123.6, 119.2, 106.7, 67.8, 31.4, 19.5, 14.0; HRMS
EI calculated for [C14H16O]+ = 200.1196, found = 200.1197.
2-Octyloxynaphthalene 4. [70617-42-4] 1H NMR (300 MHz,
CDCl3): 7.76 (m, 3H), 7.45 (m, 1H), 7.34 (m, 1H), 7.18 (m, 1H),
7.15 (s, 1H) 4.09 (t, J = 6.5 Hz, 2H), 1.86 (m, 2H), 1.56 (m, 2H),
1.37 (m, 8H), 0.92 (t, J = 7.4 Hz, 3H); 13C NMR (CDCl3): 157.3,
134.8, 129.4, 129.0, 127.7, 126.8, 126.4, 123.5, 119.2, 106.7, 68.1,
31.9, 29.6, 29.4, 26.3, 26.2, 22.8, 22.7, 14.2; HRMS EI calculated
for [C18H24O+H]+ = 257.1905, found = 257.1904.
1,7-Dibutoxynaphthalene
15. [3900-54-7]
1H
NMR
(300 MHz, CDCl3): 7.70 (m, 1H), 7.57 (m, 1H), 7.35 (m,
1H), 7.17 (m, 1H), 7.15 (m, 1H), 6.80 (m, 1H), 4.13 (m, 4H),
1.93 (m, 2H), 1.60 (m, 4H), 1.04 (m, 6H). 13C NMR (CDCl3):
156.9, 154.1, 129.9, 129.1, 126.8, 123.4, 119.9, 119.2, 105.2,
101.5, 68.0, 67.8, 31.5, 31.4, 19.6, 19.5, 14.1, 14.0. HRMS EI
calculated for [C18H24O2]+ = 272.1771, found = 272.1773.
2-(2-Methylbutoxy)naphthalene 5. 1H NMR (300 MHz,
CDCl3): 7.76 (m, 3H), 7.45 (m, 1H), 7.34 (m, 1H), 7.17 (m,
2 H), 3.95 (dd, J = 9.0 Hz, J = 6.0 Hz, 1H), 3.89 (dd, J = 9.0 Hz,
J = 6.4 Hz), 1.96 (m, 1H), 1.63 (m, 1H), 1.34 (m, 1H), 1.07 (d, J =
6.6, 3H), 0.99 (t, J = 7.4, 3H). 13C NMR (CDCl3): 157.4, 134.8,
129.4, 129.0, 127.7, 126.8, 126.4, 123.6, 119.2, 106.7, 73.0, 34.9,
26.4, 16.8, 11.5. HRMS EI calculated for [C15H18O]+ = 214.1358,
found = 214.1358.
5-Butoxynaphthalen-1-ol 16. 1H NMR (300 MHz, DMSO):
10.00 (s, 1H), 7.63 (m, 2H), 7.28 (m, 2H), 6.90 (m, 1H), 6.87 (m,
1H), 4.11 (t, J = 6.2 Hz, 2H), 1.80 (m, 2H), 1.53 (m, 2H), 0.97
(t, J = 7.3 Hz, 3 H). 13C NMR (DMSO): 154.0, 153.0, 126.4,
125.7, 125.5, 124.6, 113.9, 112.0, 108.6, 105.2, 67.3, 30.8, 18.9,
13.7. HRMS EI calculated for [C14H16O2]+ = 216.1145, found =
216.1155.
1,5-Dibutoxynaphthalene 17. [295806-76-7] 1H NMR
(300 MHz, CDCl3): 7.88 (m, 2H), 7.38 (m, 2H), 6.85 (m, 2H),
4.15 (t, J = 6.4 Hz, 4H), 1.94 (m, 4H), 1.60 (m, 4H), 1.05
(t, J = 7.4 Hz, 6 H). 13C NMR (CDCl3): 154.8, 126.9, 125.2,
114.2, 105.4, 67.9, 31.5, 19.6, 14.1. HRMS CI calculated for
[C18H24O2+H]+ = 272.1771, found = 272.1773.
2-(2-Ethylhexyloxy)naphthalene 6. 1H NMR (300 MHz,
CDCl3): 7.77 (m, 3H), 7.46 (m, 1H), 7.37 (m, 1H), 7.17 (m, 2H),
3.99 (d, J = 5.5 Hz, 2H), 1.83 (m, 1H), 1.49 (m, 8H), 0.99 (m,
6H). 13C NMR (CDCl3): 157.7, 134.9, 129.6, 129.2, 127.9, 126.9,
126.6, 123.7, 119.5, 106.8, 70.8, 39.7, 30.9, 29.46, 24.3, 23.4, 14.4,
11.5. HRMS EI calculated for [C18H24O]+ = 256.1827, found =
256.1825.
6-Butoxynaphthalen-2-ol 18. [111359-61-6] 1H NMR
(300 MHz, CDCl3): 7.62 (m, 1H), 7.57 (m, 1H), 7.10 (m, 4H),
4.05 (t, J = 6.5 Hz, 2H), 1.83 (m, 2H), 1.54 (m, 2H), 1.00 (t,
J = 7.3 Hz, 3H). 13C NMR (CDCl3): 155.7, 151.8, 129.9, 129.8,
128.5, 127.8, 119.8, 118.1, 109.8, 107.1, 67.9, 31.5, 19.5, 14.0.
HRMS CI calculated for [C14H16O2 +H]+ = 216.1145, found =
216.1155.
1
1-Butoxynaphthalene 9. [20900-19-0]; H NMR (300 MHz,
CDCl3): 8.32 (m, 1H), 7.81 (m, 1H), 7.41 (m, 4H), 6.82 (m),
4.12 (t, J = 6.3 Hz, 2H), 1.93 (m, 2H), 1.63 (m, 2H), 1.05 (t, J =
7.3 Hz, 3H); 13C NMR (CDCl3): 155.0, 134.6, 127.5, 126.4, 126.0,
125.9, 125.1, 122.2, 120.0, 104.6, 67.9, 31.5, 19.6, 14.0; HRMS
EI calculated for [C14H16O]+ = 200.1196, found = 200.1193.
This journal is
The Royal Society of Chemistry 2011
Green Chem., 2011, 13, 2482–2488 | 2487
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