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6655
3.3.1. Phenyl benzoate (2). Solid; mp 68–70 8C, (lit.18 68–
69 8C); 1H NMR (250 MHz, CDCl3): d 7.12–8.22 (m, 10H);
13C NMR (63 MHz, CDCl3): d 121.2, 125.7, 126.5, 129.5,
129.7, 131.1, 134.4, 151.5, 164.0; EI MS (m/z): 198.29;
Anal. Calcd for C13H10O2: C, 78.77; H, 5.09. Found: C,
78.73; H, 5.17.
157.6, 169.5; EI MS (m/z): 256.30; Anal. Calcd for
C16H16O3: C, 74.98; H, 6.29. Found: C, 75.09; H, 6.31.
3.3.10. Ethyl 4-phenylphenyloxy butenoate (21). Solid;
1
mp 69–70 8C; H NMR (250 MHz, CDCl3): d 1.26 (t, JZ
7.1 Hz, 3H), 4.24 (q, JZ6.9 Hz, 2H), 4.75 (d, JZ4.10 Hz,
2H), 6.15–6.8 (m, 2H), 7.15–7.52 (m, 9H); 13C NMR
(63 MHz, CDCl3): d 14.8, 60.0, 66.8, 114.1, 118.5, 128.5,
128.8, 129.6, 131.2, 142.0, 142.1, 160.4, 166.5; EIMS,
m/zZ282.34; Anal. Calcd for C18H18O3: C, 76.57; H, 6.43.
Found: C, 76.75; H, 6.35.
3.3.2. Phenyl 4-nitrobenzoate (3). Solid; mp 128–129 8C,
1
(lit.19 128–129 8C); H NMR (250 MHz, CDCl3): d 7.25–
8.42 (m, 9H); 13C NMR (63 MHz, CDCl3): d 121.2, 123.5,
126.5, 129.6, 130.1, 134,4, 150.5, 150.7, 165.0; EI MS
(m/z): 243.42; Anal. Calcd for C13H9NO4: C, 64.20; H, 3.73.
Found: C, 64.13; H, 3.75.
3.3.11. 2,6-di-tert-Butylphenyl benzyl ether (23). Liquid;
1H NMR (250 MHz, CDCl3): d 1.46 (s, 18H), 7.10–7.15 (m,
3H), 7.25–7.29 (m, 5H); 13C NMR (63 MHz, CDCl3): d
29.5, 34.8, 70.7, 122.5, 126.5, 127.4, 128.8, 132.6, 147.1,
152.8; EI MS (m/z): 296.51; Anal. Calcd for C21H28O: C,
85.08; H, 9.52. Found: C, 85.12; H, 9.40.
3.3.3. Benzyl benzoate (4). Liquid;20 1H NMR (250 MHz,
CDCl3): d 5.20 (s, 2H), 7.25–8.15 (m, 10H); 13C NMR
(63 MHz, CDCl3): d 67.4, 126.8, 129.1, 130.5, 130.8, 133.4,
135.2, 165.1; EI MS (m/z): 212.29; Anal. Calcd for
C14H12O2: C, 79.23; H, 5.70. Found: C, 79.34; H, 5.55.
3.3.12. 4-Nitrophenyl benzyl ether (24). Solid; mp 102–
1
105 8C (lit.26 105–107 8C); H NMR (250 MHz, CDCl3): d
3.3.4. 4-Phenylphenyl benzoate (8). Solid; mp 150–
152 8C, (lit.21 149–150.5 8C); 1H NMR (250 MHz,
CDCl3): d 7.10–7.38 (m, 9H), 7.41–8.15 (m, 5H); 13C
NMR (63 MHz, CDCl3) d 118.2, 121.5, 126.7, 127.5, 129.8,
130.2, 130.6, 131.9, 134.1, 138.4, 152.5, 167.0; EI MS
(m/z): 274.20; Anal. Calcd for C19H14O2: C, 83.19; H, 5.74.
Found: C, 83.20; H, 5.75.
5.25 (s, 2H), 7.04 (d, JZ9 Hz, 2H), 7.50 (s, 5H), 8.10 (d,
JZ9 Hz, 2H); 13C NMR (63 MHz, CDCl3): d 69.1, 116.9,
124.8, 126.1, 128.5, 128.8, 140.2, 141.2, 164.5; EI MS
(m/z): 229.42; Anal. Calcd for C13H11NO3: C, 68.11; H,
4.84; N, 6.11. Found: C, 67.99; H, 4.88; N, 6.12.
3.3.13. Benzyl propargyl ether (27). Liquid;31 1H NMR
(250 MHz, CDCl3): d 2.45 (t, JZ2.7 Hz, 2H) 4.12 (s, 1H),
4.5 (s, 2H), 7.10–7.22 (m, 5H); 13C NMR (63 MHz, CDCl3):
d 57.5, 72.2, 75.7, 81.4, 124.5, 127.8, 128.2, 140.2; EI MS
(m/z): 146.21; Anal. Calcd for C10H10O: C, 82.16; H, 6.89.
Found: C, 81.95; H, 6.75.
3.3.5. Methyl 4-[(2,2-dimethylpropanoyl)oxy]benzoate
(11). Liquid; 1H NMR (250 MHz, CDCl3): d 7.15 (m,
2H), 8.05 (m, 2H), 4.1 (s, 3H), 1.64 (s, 9H); 13C NMR
(63 MHz, CDCl3): d 25.6, 39.4, 51.5, 120.4, 127.7, 130.8,
157.8, 165.2, 174.1; EI MS (m/z): 236.27; Anal. Calcd for
C13H16O4: C, 66.09; H, 6.83. Found: C, 66.12; H, 6.85.
3.3.14. 2-Allylphenyl 4-methoxybenzyl ether (28). Liquid;
1H NMR (250 MHz, CDCl3): d 3.05 (m, 2H), 3.74 (s, 3H),
5.12 (s, 2H), 5.22–5.28 (m, 2H), 6.20–6.25 (m, 1H), 6.80–
7.45 (m, 8H); 13C NMR (63 MHz, CDCl3): d 36.5, 54.01,
70.1, 112.8, 114.9, 115.4, 121.8, 126.1, 127.4, 129.8, 138.2,
157.5, 159.2; EI MS (m/z): 254.28; Anal. Calcd for
C17H18O2: C, 80.28; H, 7.13. Found: C, 80.24; H, 7.15.
3.3.6. Benzyl phenyl ether (13). Solid; mp 39–40 8C (lit.24
1
38 8C); H NMR (250 MHz, CDCl3): d 5.20 (s, 2H, CH2),
6.77–6.19 (m, 10H); 13C NMR (63 MHz, CDCl3): d 70.10,
114.1, 123.8, 127.5, 127.9, 128.4, 129.5, 137.6, 158.1; EI
MS (m/z): 184.24; Anal. Calcd for C13H12O: C, 84.75; H,
6.57. Found: C, 84.59; H, 6.65.
3.3.7. 4-Nitrobenzyl phenyl ether (15). Solid; mp 90–
91 8C (lit.26 89–91 8C); 1H NMR (250 MHz, CDCl3): d 5.22
(s, 2H), 7.05 (m, 3H), 7.50 (m, 2H), 7.24 (d, JZ9 Hz, 2H),
7.95 (d, JZ9 Hz, 2H); 13C NMR (63 MHz, CDCl3): d 70.1,
114.9, 121.8, 124.1, 126.5, 129.8, 138.1, 146.7, 158.2; EI
MS (m/z): 229.55; Anal. Calcd for C13H11NO3: C, 68.11; H,
4.84. Found: C, 67.97; H, 4.96.
Acknowledgements
We express our gratitude to Deutscher Akademischer
Austauschdienst (DAAD, Bonn, Germany) for a scholar-
ship, granted to Syed Tasadaque Ali Shah.
3.3.8. 3,5-Dimethoxyphenyl propionitrile ether (17).
1
Liquid; H NMR (250 MHz, CDCl3): d 2.82 (t, JZ6.2 Hz,
References and notes
2H), 3.58 (s, 6H), 4.22 (t, JZ6.7 Hz, 2H) 6.24–6.32 (m,
3H); 13C NMR (63 MHz, CDCl3): d 18.5, 55.2, 64.1, 92.6,
100.7, 118.1, 161.4, 164.6; EI MS (m/z): 207.24; Anal.
Calcd for C11H13NO3: C, 63.76; H, 6.32. Found: C, 63.78;
H, 6.41.
1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic
Synthesis; Wiley-Interscience: New York, 1991; and
numerous references quoted therein.
2. Lee, J. C.; Choi, Y. Synth. Commun. 1998, 28, 2021–2026.
3. Khan, K. M.; Hayat, S.; Zia-Ullah; Atta-ur-Rahman; Choudhary,
M. I.; Maharvi, G. M.; Bayer, E. Synth. Commun. 2003, 33,
3435–3453.
3.3.9. Ethyl 4-phenylphenoxy acetate (20). Solid; mp 60–
1
61 8C, (lit.29 60 8C); H NMR (250 MHz, CDCl3): d 1.36
(t, JZ6.7 Hz, 3H), 4.24 (q, JZ6.9 Hz, 2H), 4.85 (s, 2H),
6.75–7.52 (m, 9H); 13C NMR (63 MHz, CDCl3): d 14.2,
61.1, 65.0, 115.8, 127.6, 128.2, 128.8, 129.4, 130.4, 142.5,
4. Hayat, S.; Atta-ur-Rahman; Choudhary, M. I.; Khan, K. M.;
Schumann, W.; Bayer, E. Tetrahedron 2001, 57, 9951–9957.