G. Asensio et al.
8.4 Hz), 4.37 (s, 2H), 3.73 (s, 3H), 3.23 (d, J=7.1 Hz, 2H), 2.00 (sept.,
J=7.5 Hz, 1H), 1.61–1.70 (m, 2H), 1.41–1.42 (m, 4H), 1.12–1.21 ppm (m,
2H); 13C NMR (CDCl3): d=159.1, 131.0, 129.2, 113.8, 74.8, 72.6, 55.3,
39.5, 29.7, 25.5 ppm; HMRS (EI): m/z: calcd for C13H14O: 220.1463 [M]+;
found: 220.1469.
J=6.1 Hz, 1H), 3.61 (sept, J=6.0 Hz, 1H), 2.64–2.74 (m, 1H), 2.24–2.35
(m, 1H), 1.84–1.93 (m, 2H), 1.56–1.68 (m, 4H), 1.46–1.51 (m, 4H), 1.31–
1.38 ppm (m, 2H); 13C NMR (CDCl3): d=143.9, 143.2, 127.8, 126.3,
124.7, 124.6, 80.8, 78.9, 35.1, 34.2, 33.6, 29.9, 28.4, 28.2, 23.0, 22.8 ppm;
HMRS (EI): m/z: calcd for C16H22O: 230.1670 [M]+; found: 230.1668.
1-Methoxy-4-(neopentyloxymethyl)benzene (3ab): Yield: 58%; colour-
less oil; 1H NMR (CDCl3): d=7.18 (d, J=8.4 Hz), 6.78 (d, J=8.4 Hz),
4.38 (s, 2H), 3.73 (s, 3H), 3.01 (s, 2H), 0.84 ppm (s, 9H); 13C NMR
(CDCl3): d=158.8, 131.1, 128.8, 113.6, 80.5, 72.8, 55.2, 32.0, 26.7 ppm;
HMRS (EI): m/z: calcd for C13H20O: 208.1463 [M]+; found: 208.1463.
(Isopropoxymethylene)dibenzene (3cf): Yield: 56%; colourless oil;
1H NMR (CDCl3): d=7.15–7.32 (m, 10H), 5.43 (s, 1H), 3.62 (sept., J=
6 Hz, 1H); 1.16 ppm (d, J=6 Hz, 6H); 13C NMR (CDCl3): d=142.2,
128.2, 127.2, 127.0, 80.4, 69.0, 22.2 ppm; HMRS (EI): m/z: calcd for
C16H18O: 226.1357 [M]+; found: 226.1362.
(1-Isopropoxyethyl)benzene (3ef): Yield: 53%; colourless oil; 1H NMR
(CDCl3): d=7.20–7.30 (m, 8H), 4.50 (q, J=6 Hz, 1H), 3.44 (sept., J=
6 Hz, 1H), 1.37 (d, J=6 Hz, 3H), 1.11 (d, J=6 Hz, 3H), 1.06 ppm (d, J=
6 Hz, 3H); 13C NMR (CDCl3): d=144.8, 128.2, 127.1, 126.0, 74.5, 68.4,
24.7, 23.3, 21.3 ppm; HMRS (EI): calcd for C8H9O: 121.0653 [MÀ43]+;
found: 121.0640.
1-(Isopentyloxymethyl)-4-methoxybenzene (3ac): Yield: 60%; colourless
oil; H NMR (CDCl3): d=7.19 (d, J=8.4 Hz), 6.80 (d, J=8.4 Hz), 4.36 (s,
2H), 3.73 (s, 3H), 3.39 (t, J=6.7 Hz, 2H), 1.65 (sept., J=6.6 Hz, 1H),
1.42 (m, 2H), 0.82 ppm (d, J=6.6 Hz, 6H); 13C NMR (CDCl3): d=159.0,
130.7, 129.1, 113.7, 72.5, 68.5, 55.2, 38.5, 25.0, 22.6 ppm; HMRS (EI):
calcd for C13H20O: 208.1463 [M]+; found: 208.1463.
1
(9-Isopropoxy)fluorene (3 ff): Yield: 58%; colourless oil; 1H NMR
(CDCl3): d=7.53–7.59 (m, 4H), 7.18–7.33 (m, 4H), 5.50 (s, 1H), 3.74
(sept., J=6 Hz, 1H), 1.13 ppm (d, J=6 Hz, 6H); 13C NMR (CDCl3): d=
144.3, 140.4, 128.7, 127.4, 125.4, 119.8, 79.7, 69.9, 23.7 ppm; HMRS (EI):
m/z: calcd for C16H16O: 224.1201 [M]+; found: 224.1202.
1-(Ethoxymethyl)-4-methoxybenzene (3ad): Yield: 61%; colourless oil;
1H NMR (CDCl3): d=7.19 (d, J=8.4 Hz), 6.78 (d, J=8.4 Hz), 4.20 (q,
J=7.0 Hz, 2H), 3.71 (s, 3H), 1.15 ppm (t, J=7.0 Hz, 1H); 13C NMR
(CDCl3): d=158.7, 132.0, 128.7, 113.6, 72.7, 65.8, 55.6, 15.6 ppm; HMRS
(EI): calcd for C10H14O: 166.0993 [M]+; found: 166.0983.
[3-(tert-Pentyloxy)propyl]benzene (3hj): Yield: 23%; colourless oil;
1H NMR (CDCl3): d=7.07–7.22 (m, 5H), 3.25 (t, J=6.4 Hz, 2H), 2.61 (t,
J=7.8 Hz, 2H), 1.73–1.82 (m, 2H), 1.42 (q, J=7.5 Hz, 2H), 1.05 (s, 6H),
0.80 ppm (t, J=7.5 Hz, 3H); 13C NMR (CDCl3): d=142.3, 128.4, 128.2,
125.5, 74.4, 60.2, 32.7, 32.5, 32.1, 25.0, 8.2 ppm; HMRS (EI): m/z: calcd
for C14H22O: 205.1592 [M]+; found: 205.1548.
1-Methoxy-4-(pentyloxymethyl)benzene (3ae): Yield: 58%; colourless
oil; H NMR (CDCl3): d=7.18 (d, J=8.4 Hz), 6.79 (d, J=8.4 Hz), 4.35 (s,
2H), 3.72 (s, 3H), 3.36 (t, J=6.7 Hz, 2H), 1.50–1.55 (m, 2H), 1.23–1.28
(m, 4H), 0.79–0.84 ppm (m, 3H); 13C NMR (CDCl3): d=159.0, 130.7,
129.1, 113.6, 72.4, 70.1, 55.2, 29.4, 28.3, 22.5, 14.0 ppm; HMRS (EI): calcd
for C13H20O: 208.1463 [M]+; found: 208.1457.
1
1
(3-tert-Butoxypropyl)benzene (3gj): Yield: 40%; colourless oil; H NMR
1-(Isopropoxymethyl)-4-methoxybenzene (3af): Yield: 71%; colourless
oil; 1H NMR (CDCl3): d=7.19 (d, J=8.4 Hz), 6.79 (d, J=8.4 Hz), 4.3 (s,
2H), 3.71 (s, 3H), 3.58 (sept., J=6.1 Hz, 1H), 1.12 ppm (t, J=6.1 Hz,
6H); 13C NMR (CDCl3): d=158.9, 131.1, 129.0, 113.6, 70.5, 69.6, 55.2,
22.0 ppm; HMRS (EI): calcd for C11H16O: 180.1150 [M]+; found:
180.1146.
(CDCl3): d=7.09–7.24 (m, 4H), 3.30 (t, J=6.4 Hz, 2H), 2.63 (t, J=
8.1 Hz, 2H), 1.75–1.85 (m, 2H), 1.13 ppm (s, 9H); 13C NMR (CDCl3): d=
142.2, 128.4, 128.2, 125.6, 72.5, 60.7, 32.4, 32.1, 27.6 ppm; HMRS (EI):
calcd for C12H17O: 177.1279 [MÀ15]+; found: 177.1259.
1-(tert-Butoxymethyl)-4-methoxybenzene (3ag): Yield: 76%; colourless
1
oil; H NMR (CDCl3): d=7.18 (d, J=8.4 Hz), 6.79 (d, J=8.4 Hz), 4.30 (s,
2H), 3.71 (s, 3H), 1.21 ppm (s, 9H); 13C NMR (CDCl3): d=158.8, 131.9,
128.9, 113.7, 73.2, 63.7, 55.3, 27.7 ppm; HMRS (EI): calcd for C12H18O:
194.1306 [M]+; found: 194.1297.
Acknowledgements
Financial support by the Spanish Dirección General de Investigación,
Consolider Ingenio 2010 (CSD2007—00006) and the Generalitat Valenci-
ana 842/2005 and 027/2005) is gratefully acknowledged. We acknowledge
SCSIE (Universidad de Valencia) for access to instrumental facilities.
1-Methoxy-4-(tert-pentyloxymethyl)benzene (3ah): Yield: 58%; colour-
less oil; 1H NMR (CDCl3): d=7.19 (d, J=8.4 Hz), 6.78 (d, J=8.4 Hz),
4.20 (s, 2H), 3.71 (s, 3H), 1.52 (q, J=7.5 Hz, 1H), 1.15 (s, 6H), 0.85 ppm
(t, J=7.5 Hz, 3H); 13C NMR (CDCl3): d=158.7, 132.0, 128.7, 113.6, 75.2,
63.2, 55.2, 32.7; 25.2, 8.3 ppm; HMRS (EI): calcd for C13H20O: 208.1463
[M]+; found: 208.1461.
ner, P. W. Davies, Angew. Chem. 2007, 119, 3478–3519; Angew.
Chem. Int. Ed. 2007, 46, 3410–3449; c) A. S. K. Hashmi, G. J. Hutch-
[2] W. H. Miles, K. B. Connell, J. Chem. Educ. 2006, 83, 285–286.
[3] a) M. Pagliaro, R. Ciriminna, H. Kimura, M. Rossi, C. Della Pina,
46, 4434–4440; b) G. D. Yadav, V. V. Bokade, Appl. Catal. A 1996,
147, 299–323.
[4] a) J. March, Advanced Organic Chemsitry, Reactions, Mechanism
and Structure, 4th ed., Wiley, New York 1992, pp. 386–387; b) J.
March, Advanced Organic Chemsitry, Reactions, Mechanism and
Structure, 4th ed., Wiley, New York 1992, pp. 389–390.
[5] J. Barluenga, L. Alonso-Cires, P. J. Campos, G. Asensio, Synthesis
1-(Cyclopentylmethoxy)-2,3-dihydro-1H-indene (3ba): Yield: 83%; col-
ourless oil; 1H NMR (CDCl3): d=7.11–7.32 (m, 4H), 4.18–4.85 (m, 1H),
3.26–3.37 (m, 2H), 2.29–3.03 (m, 1H), 2.62–2.76 (m, 1H), 2.21–2.32 (m,
1H), 2.05–2.15 (m, 1H), 1.91–2.02 (m, 1H), 1.62–1.72 (m, 2H), 1.44–1.51
(m, 4H), 1.16–1.21 ppm (m, 2H); 13C NMR (CDCl3): d=143.6, 143.1,
128.0, 126.2, 124.9, 124.7, 83.1, 73.2, 39.6, 32.3, 30.1, 29.6, 29.6, 25.3 ppm;
HMRS (EI): calcd for C15H20O: 216.1514 [M]+; found: 216.1515.
1-Ethoxy-2,3-dihydro-1H-indene (3bd): Yield: 47%; colourless oil;
1H NMR (CDCl3): d=7.31–7.33 (m, 2H), 7.10–7.18 (m, 2H), 4.48 (dd,
J=6.6, 4.3 Hz, 1H), 3.53 (q, J=7.0 Hz, 2H), 2.95–3.06 (m, 1H), 2.68–2.78
(m, 1H), 2.22–2.33 (m, 1H), 1.94–2.04 (m, 1H), 1.15 ppm (t, J=6.9 Hz,
3H); 13C NMR (CDCl3): d=143.8, 143.0, 128.1, 126.2, 124.9, 124.8, 82.9,
63.9, 32.4, 30.1, 15.5 ppm; HMRS (EI): m/z: calcd for C11H14O: 162.1044
[M]+; found: 162.1050.
1-Isopropoxy-2,3-dihydro-1H-indene (3bf): Yield: 96%; colourless oil;
1H NMR (CDCl3): d=7.27–7.30 (m, 1H), 7.10–7.17 (m, 3H), 4.91 (t, J=
6.2 Hz, 1H), 3.78 (sept., J=6.1 Hz, 1H), 2.92–3.02 (m, 1H), 2.71 (quint.,
J=7.7 Hz, 1H), 2.25–2.36 (m, 1H), 1.86–1.97 (m, 1H), 1.15 ppm (dd, J=
6.1, 1.0 Hz, (6H); 13C NMR (CDCl3): d=143.8, 143.3, 127.9, 126.3, 124.7,
124.6, 80.9, 70.2, 33.6, 29.9, 23.1, 22.5 ppm; HMRS (EI): calcd for
C12H16O: 176.1201 [M]+; found: 176.1204.
1-(Cycloheptyloxy)-2,3-dihydro-1H-indene (3bi): Yield: 86%; colourless
oil; 1H NMR (CDCl3): d=7.26–7.29 (m, 1H), 7.11–7.16 (m, 3H), 4.90 (t,
[10] K. J. Millar, M. M. Abu-Omar, Eur. J. Org. Chem. 2003, 1294–1299.
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ꢀ 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2008, 14, 1518 – 1523