Table 3 Simulation settings and physical properties of liquids used for
the simulations
175 (62), 147 (10), 127 (49), 70 (100); HRMS (EI) m/z calcd. for
C13H13F3O [M+-2H]: 242.0913, found: 242.0912.
Property
Value
2,2-Dimethyl-1-naphthalen-2-yl-but-3-en-1-ol (3c). Pale yellow
oil; 1H NMR (270 MHz, CDCl3): d 7.84–7.74 (m, 4H), 7.48–7.42
(m, 3H), 5.97 (dd, J = 17.6, 10.8 Hz, 1H), 5.18–5.06 (m, 2H), 4.60
(s, 1H), 2.14 (bs, 1H), 1.06 (s, 3H), 1.01 (s, 3H); MS (EI) m/z
(relative intensity): 226 ([M+], 4.6), 157 (100), 129 (92), 102 (3), 77
(6).
Mesh number
1 046 000
Inlet velocity (Inflow 1 and Inflow 2)
Mass fraction of benzaldehyde (Inflow 1)
Mass fraction of benzaldehyde (Inflow 2)
Molecular weight (HMPA)
Molecular weight (benzaldehyde)
Density (HMPA)
8.33 ¥ 10-4 m s-1
0
0.206
179.2 kg kmol-1
106.12 kg kmol-1
1030 kg m-3
1041.5 kg m-3
1.11 ¥ 10-2 Pa s
4-Methyl-1-naphthalen-2-yl-pent-3-en-1-ol (4c). Pale yellow
Density (benzaldehyde)
1
Dynamic viscositya
oil; H NMR (270 MHz, CDCl3): d 7.84–7.81 (m, 4H), 7.51–
7.42 (m, 3H), 5.23–5.16 (m, 1H), 4.85 (dd, J = 7.6, 5.4 Hz, 1H),
2.58–2.51 (m, 2H), 2.11 (bs, 1H), 1.73 (s, 3H), 1.63 (s, 3H); MS
(EI) m/z (relative intensity): 226 ([M+], 5.1), 208 (12), 193 (21),
178 (16), 157 (100), 129 (96), 115 (4), 89 (5), 77 (6).
a Obtained by rheology measurements of Fig. 5.
presumed. A no-slip boundary condition was used at the walls
where the velocity is zero.
2,2-Dimethyl-1-p-tolyl-but-3-en-1-ol (3d). Colorless oil; 1H
NMR (270 MHz, CDCl3): d 7.20–7.10 (m, 4H), 5.92 (dd, J =
17.5, 10.9 Hz, 1H), 5.15–5.04 (m, 2H), 4.40 (s, 1H), 2.34 (s, 3H),
1.01 (s, 3H), 0.95 (s, 3H); MS (EI) m/z (relative intensity): 190
([M+], 0.29), 121 (100), 93 (81), 77 (64), 70 (69).
Acknowledgements
This work was financially supported in part by the Global COE
Program (Tokyo Institute of Technology, Education and Research
Center for Emergence of New Molecular Chemistry) and a Grant-
in-Aid for JSPS Fellows from the Japanese Ministry of Education,
Culture, Sports, Science and Technology.
4-Methyl-1-p-tolyl-pent-3-en-1-ol (4d). Colorless oil; 1H NMR
(270 MHz, CDCl3): d 7.25 (d, J = 8.07 Hz, 2H), 7.15 (d, J = 8.07
Hz, 2H), 5.20–5.14 (m, 1H), 4.64 (dd, J = 7.91 Hz, 5.27, 1H),
2.58–2.29 (m, 2H), 2.34 (s, 3H), 1.94 (bs, 1H), 1.73 (s, 3H), 1.62
(s, 3H); MS (EI) m/z (relative intensity): 190 ([M+], 1.3), 172 (10),
157 (16), 142 (11), 121 (100), 93 (80), 77 (57), 70 (58).
Notes and references
1-Furan-3-yl-2,2-dimethyl-but-3-en-1-ol (3e). Yellow oil; 1H
NMR (270 MHz, CDCl3): d 7.36–7.7.34 (m, 2H), 6.37–6.36 (m,
1H), 5.91 (dd, J = 17.3, 10.8 Hz, 1H), 5.17–5.07 (m, 2H), 4.40 (s,
1H), 1.03 (s, 3H), 1.00 (s, 3H); MS (EI) m/z (relative intensity):
166 ([M+, 8]), 133 (1), 97 (100), 70 (90).
1 (a) K. Matsuda, M. Atobe and T. Nonaka, Chem. Lett., 1994, 1619;
(b) M. Atobe and T. Nonaka, Chem. Lett., 1995, 669; (c) M. Atobe, K.
Matsuda and T. Nonaka, Electroanalysis, 1996, 8, 784; (d) M Atobe
and T. Nonaka, J. Electroanal. Chem., 1997, 425, 161.
2 M. Iannelli, V. Alupei and H. Ritter, Tetrahedron, 2005, 61, 1509.
3 (a) B. J. Cohen, M. A. Kraus and A. Patchornik, J. Am. Chem. Soc.,
1977, 99, 4165; (b) B. Helms, S. J. Guillaudeu, Y. Xie, M. McMurdo, C.
J. Hawker and J. M. J. Fre´chet, Angew. Chem., Int. Ed., 2005, 44, 6384;
(c) T. Tajima and A. Nakajima, J. Am. Chem. Soc., 2008, 130, 10496.
4 (a) G. Jas and A. Kirschning, Chem.–Eur. J., 2003, 9, 5708; (b) S. Suga,
A. Nagaki and J. Yoshida, Chem. Commun., 2003, 354; (c) A. Nagaki,
H. Kim and J. Yoshida, Angew. Chem., Int. Ed., 2009, 48, 8063; (d) D.
Webb and T. F. Jamison, Chem. Sci., 2010, 1, 675.
5 For selected books and reviews on microreactor technology, see:
(a) Microreaction Technology, ed. W. Ehrfeld, Springer, Berlin, 1998;
(b) S. J. Haswell, P. D. I. Fletcher, G. M. Greenway, V. Skelton, P.
Styring, D. O. Morgan, S. Y. F. Wong and B. H. Warrington, in
Automated Synthetic Methods for Speciality Chemicals, ed. W. Hoyle,
Royal Society of Chemistry, Cambridge, 1999, p. 26; (c) Microsystem
Technology in Chemistry and Life Sciences, ed. A. Manz and H. Becker,
Springer, Berlin, 1999; (d) Microreactors, ed. W. Ehrfeld, V. Hessel and
H. Lo¨we, Wiley-VCH, Weinheim, 2000; (e) K. F. Jensen, Chem. Eng.
Sci., 2001, 56, 293; (f) S. J. Haswell, R. J. Middleton, B. O’Sullivan,
V. Skelton, P. Watts and P. Styring, Chem. Commun., 2001, 391; (g) P.
D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P.
Watts, S. Y. F. Wong and X. Zhang, Tetrahedron, 2002, 58, 4735; (h) K.
Ja¨hnisch, V. Hessel and H. Lo¨we, Angew. Chem., Int. Ed., 2004, 43,
406; (i) J. Yoshida, A. Nagaki, T. Iwasaki and S. Suga, Chem. Eng.
Technol., 2005, 28, 259; (j) K. Geyer, J. D. C. Code´e and P. H. Seeberger,
Chem.–Eur. J., 2006, 12, 8434; (k) A. J. deMello, Nature, 2006, 442,
394; (l) B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan and
D. T. McQuade, Chem. Rev., 2007, 107, 2300; (m) J. Yoshida and S.
Suga, Electrochemistry, 2007, 75, 58; (n) J. Yoshida, A. Nagaki and
T. Yamada, Chem.–Eur. J., 2008, 14, 7450; (o) T. Fukuyama, Md. T.
Rahman, M. Sato and I. Ryu, Synlett, 2008, 2, 151; (p) F. E. Valera, M.
Quaranta, A. Moran, J. Blacker, A. Armstrong, J. T. Cabral and D. G.
Blackmond, Angew. Chem., Int. Ed., 2010, 49, 2478.
1-Furan-3-yl-4-methyl-pent-3-en-1-ol (4e). Yellow oil; 1H
NMR (270 MHz, CDCl3): d 7.39–7.37 (m, 2H), 6.42–6.41 (m,
1H), 5.20–5.12 (m, 1H), 4.66 (dd, J = 7.26, 5.79 Hz, 1H), 2.55–
2.37 (m, 2H), 1.85 (bs, 1H), 1.73 (s, 3H), 1.65 (s, 3H); MS (EI) m/z
(relative intensity): 166 ([M+], 10.9), 148 (4.4), 133 (3.5), 119 (4.1),
97 (100), 70 (95).
CFD simulation settings
A T-type planer (2D) geometry and boundary conditions used
are shown in Fig. 13. The quadrilateral mesh was generated by
using the pre-processor Gambit 2.4 software (ANSYS Inc.). The
physical properties and simulation parameters used in the present
work are listed in Table 3. A uniform inlet velocity was set at the
two inlets and input streams were assumed to develop into laminar
flows. In application of Fluent 6.3, Navier–Stokes equations
and species transport equations were solved simultaneously. No
heat transfer and no reaction between transported species were
6 S. Suga, D. Yamada and J. Yoshida, Chem. Lett., 2010, 39, 404.
7 F. Amemiya, K. Fuse, T. Fuchigami and M. Atobe, Chem. Commun.,
2010, 46, 2730.
Fig. 13 Schematic illustration of the geometry and the boundary
conditions used in the CFD simulation.
4264 | Org. Biomol. Chem., 2011, 9, 4256–4265
This journal is
The Royal Society of Chemistry 2011
©