1,3-Bis(4-nitrile-benzyloxy)propane (8c)
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1
Colorless oil. TLC: Rf 0.44 (cyclohexane/EtOAc = 2/1); H
NMR (300 MHz, CDCl3): d = 7.63 (d, J = 8.2 Hz, 4H), 7.42 (d,
J = 8.1 Hz, 4H), 4.55 (s, 4H), 3.63 (t, J = 6.2 Hz, 4H), 1.96 (p,
J = 6.3 Hz, 2H).
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3-Hydroxypropyl 4-((3-hydroxypropoxy)methyl)benzoate (9b)
White Solid. TLC: Rf 0.25 (cyclohexane/EtOAc = 1/4); 1H
NMR (300 MHz, CDCl3): d = 8.02 (d, J = 8.3 Hz, 2H), 7.40
(d, J = 8.2 Hz, 2H), 4.58 (s, 2H), 4.49 (t, J = 6.2 Hz, 2H),
4.63–4.41 (m, 6H), 2.09–1.96 (m, 2H), 1.96–1.83 (m, 2H); 13C
NMR (101 MHz, CDCl3): d = 167.1, 143.9, 130.1, 129.7, 127.5,
72.9, 69.8, 62.1, 61.8, 59.4, 32.5, 32.2; HRESI MS: calcd for
C14H20NaO5 ([M+Na]+) 291.1208, found 291.1205.
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4-(Methoxymethyl)benzonitrile (10b)
White oil.1H NMR (300 MHz, CDCl3): d = 7.60 (d, J = 8.3 Hz,
2H), 7.41 (d, J = 8.3 Hz, 2H), 4.48 (s, 2H), 3.39 (s, 3H); 13C
NMR (75 MHz, CDCl3): d = 143.9, 132.0, 127.6, 118.6, 111.0,
73.4, 58.4.
Methyl 4-(methoxymethyl)benzoate (11b)
10 M. A. Brook, Silicon in Organic, Organometallic and Polymer
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Colorless oil.1H NMR (300 MHz, CDCl3): d = 8.04 (d, J =
8.0 Hz, 2H), 7.41 (d, J = 7.9 Hz, 2H), 4.52 (s, 2H), 3.92 (s, 3H),
3.42 (s, 3H); 13C NMR (75 MHz, CDCl3): d = 166.9, 143.5, 129.7,
129.3, 127.2, 74.0, 58.3, 52.0.
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3-(Dodecyloxy)propane-1,2-diol (12b)23
Colorless oil. 1H NMR (300 MHz, CDCl3): d = 3.93–3.82
(m, 1H), 3.81–3.63 (m, 2H), 3.60–3.38 (m, 4H), 1.74–1.51 (m,
2H), 1.36–1.12 (m, 18H), 0.85 (t, J = 6.7 Hz, 3H); 13C NMR
(101 MHz, CDCl3): d = 72.6, 72.1, 71.0, 64.4, 32.2, 30.0, 29.9,
29.8, 29.8, 29.6, 26.4, 23.0, 14.4.
3-Hydroxypropyl 4-(1,3-dioxan-2-yl)benzoate (9a)
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16 R. Thomas, Money Week, 2010, 106, 9–11.
To a solution of methyl 4-formylbenzoate (2.0 g, 12.2 mmol)
in 25 mL propane-1,3-diol,
5 mol% of CSA (1R-10-
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camphorsulfonic acid) was added. After stirring for 16 h at
80 ◦C, the mixture was diluted with CH2Cl2, washed with
water, dried over MgSO4, filtered and concentrated. Silica
column chromatography afforded 9a as a white◦solid. TLC:
Rf 0.20 (cyclohexane/EtOAc = 3/2); mp = 101.8 C;1H NMR
(300 MHz, CDCl3) d 8.09–7.95 (m, 2H), 7.64–7.44 (m, 2H), 5.53
(s, 1H), 4.45 (t, J = 6.2 Hz, 2H), 4.27 (dd, J = 11.2, 4.7 Hz, 2H),
4.07–3.88 (m, 2H), 3.74 (t, J = 6.1 Hz, 2H), 2.35–2.08 (m, 2H),
2.05–1.87 (m, 2H); 13C NMR (101 MHz, CDCl3): d = 166.9,
143.6, 130.5, 129.8, 126.3, 100.9, 67.6, 61.9, .59.3, 32.0, 25.9;
HRESI MS: calcd for C14H18NaO5 ([M+Na]+) 289.1052, found
289.1047.
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Acknowledgements
China Scholarship Council is warmly thanked for PhD grants
to Yin-Jie Zhang.
Notes and references
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Werz, H. J. Schuster and L. F. Tietze, Synlett, 2008, 13, 1969–1972.
2742 | Green Chem., 2011, 13, 2737–2742
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