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E. Kowalska, P. Bałczewski / Ultrasonics Sonochemistry 34 (2017) 743–753
2.3.6. 6-(3,4,5-Trimethoxybenzyl)benzo[d][1,3]dioxole-5-carbaldehyde
(3f)
2.3.11. Anthracene (4a)
Yield: 78%. Yellow solid; m.p. >200 °C; IR (KBr) cmÀ1: 3048,
2923, 2853, 1620, 1532, 1447, 1315, 1271, 1146, 997, 956, 883,
726, 601; 1H NMR (CDCl3, 200 MHz): d (ppm) = 7.42–7.49 (m, 4H,
4xHAr), 7.96–8.03 (m, 4H, 4xHAr), 8.42 (s. 2H, 2xHAr); 13C NMR
Yield: 91%. White solid; m.p. 110 °C; 1H NMR (CDCl3, 500 MHz):
d (ppm) = 3.78 (s, 6H, 2xOCH3), 3.80 (s, 3H, OCH3), 4.28 (s, 2H, CH2),
6.04 (s, 2H, OCH2O), 6.33 (s, 2H, 2xHAr), 6.68 (s, 1H, HAr), 7.34 (s,
1H, HAr), 10.15 (s, 1H, CHO); 13C NMR (CDCl3, 125 MHz): d
(ppm) = 37.53, 55.88, 55.88, 60.64, 101.83, 105.39, 105.39,
108.75, 110.79, 128.27, 135.65, 136.32, 140.13, 146.82, 152.32,
153.16, 153.16, 189.41; HRMS (EI, 70 eV): m/z [M]+ Calcd for:
(CDCl3, 50 MHz):
d (ppm) = 124.07, 124.07, 124.07, 124.07,
124.94, 124.94, 126.89, 126.89, 126.89, 126.89, 130.39, 130.39,
130.39, 130.39; HRMS (EI, 70 eV): m/z [M]+ Calcd for C14H10
:
178.07825; Found: 178.07811; MS (EI, 70 eV) m/z (%) 178 [M+,
100]; Anal. calcd for C14H10: C, 94.34; H, 5.66; Found: C, 94.42;
H, 5.59.
C
18H18O6: 330.11034; Found: 330.11027; MS (EI, 70 eV) m/z (%)
330 [M+, 100], 313 [M+, –OH, 35], 299 [M+, –CH2O, –H, 49], 282
[M+, -OMe, –OH, 29], 266 [M+, –Me, –OMe, –CHO, 25], 240
[M+, –CHO, -2xMe, –OCH3, 15], 196 [M+, –CHO, –C6H2(OMe)3, 35];
Anal. calcd for C18H18O6: C, 65.45; H, 5.49; Found: C, 65.42; H, 5.57.
2.3.12. Tetraphene (4b)
Yield: 81%. Yellow solid; m.p. 154 °C; IR (KBr) cmÀ1: 3047, 2923,
2853, 1623, 1499, 1475, 1338, 1238, 954, 897, 885, 812, 746, 688;
1H NMR (CDCl3, 200 MHz): d (ppm) = 7.50–7.88 (m, 7H, 7xHAr),
8.00–8.15 (m, 2H, 2xHAr), 8.35 (s, 1H, HAr), 8.82 (d, 1H,
3JH–H = 8.0 Hz, HAr), 9.16 (s, 1H, HAr); 1H NMR (CDCl3, 500 MHz): d
(ppm) = 7.53–7.60 (m, 2H, 2xHAr), 7.61–7.67 (m, 2H, 2xHAr), 7.70
2.3.7. 4-Methoxy-2-(3,4,5-trimethoxybenzyl)benzaldehyde (3g)
Yield: 93%. White solid; m.p. 100 °C; 1H NMR (CDCl3, 500 MHz):
d (ppm) = 3.72 (s, 6H, 2xOCH3), 3.76 (s, 3H, OCH3), 3.79 (s, 3H,
OCH3), 4.26 (s, 2H, CH2), 6.29 (s, 2H, 2xHAr), 7.05 (d, 1H,
3
3
4
3JH–H = 10.0 Hz, HAr), 7.15 (d, 1H, JH–H = 10.0 Hz, HAr), 7.34 (s, 1H,
(dt, 1H, JH–H = 10.0 Hz, JH–H = 5.0 Hz, HAr), 7.80 (d, 1H,
4
H
Ar), 10.18 (s, 1H, CHO); 13C NMR (CDCl3, 125 MHz):
d
3JH–H = 10.0 Hz, HAr), 7.87 (d, 1H, JH–H = 5.0 Hz, HAr), 8.03–8.17
4
(ppm) = 37.04, 55.22, 55.76, 55.76, 60.55, 105.37, 105.37, 114.21,
120.50, 132.54, 134.43, 134.89, 136.09, 136.32, 153.04, 153.04,
158.33, 191.54; HRMS (EI, 70 eV): m/z [M]+ Calcd for C18H20O5:
316.13107; Found: 316.13061; MS (EI, 70 eV) m/z (%) 316
(M+, 100), 298 [M+, –H2O, 39], 285 [M+, –CH2O, –H, 60], 226
[M+, -4xMe, –CH2O, 23], 120 [M+, -Me, C6H2(OMe)3, 28]; Anal. calcd
for C18H20O5: C, 68.34; H, 6.37; Found C, 68.42; H, 6.45.
(m, 2H, 2xHAr), 8.37 (s, 1H, HAr), 8.85 (d, 1H, JH–H = 5.0 Hz, HAr),
9.17 (s, 1H, HAr); 13C NMR (CDCl3, 125 MHz): d (ppm) = 121.62,
123.01, 125.77, 125.88, 125.88, 126.85, 126.92, 127.15, 127.41,
127.41, 127.82, 127.82, 128.52, 128.69, 128.92, 130.60, 131.98,
132.04; HRMS (EI, 70 eV): m/z [M]+ calcd for C18H12: 228.09390;
Found: 228.09323; MS (EI, 70 eV) m/z (%) 228 [M+, 100]; Anal. calcd
for C18H12: C, 94.70; H, 5.30; Found: C, 94.58; H, 5.57.
2.3.8. 3-Benzylthiophene-2-carbaldehyde (3h)
2.3.13. Tetrapheno[9,10-d][1,3]dioxole (4c)
Yield: 64%. Light yellow oil; 1H NMR (CDCl3, 600 MHz): d
(ppm) = 4.33 (s, 2H, CH2), 6.94 (d, 1H, HAr), 7.20 (s, 1H, HAr), 7.21
(s, 1H, HAr), 7.23–7.25 (m, 1H, HAr), 7.31–7.33 (m, 2H, 2xHAr),
7.61 (d, 1H, HAr); 13C NMR (CDCl3, 150 MHz): d (ppm) = 34.14,
126.60,128.54, 128.72, 128.72, 131.33, 131.33, 134.54, 137.95,
139.07, 149.92, 182.28; HRMS (EI, 70 eV): m/z [M]+ Calcd for
Yield: 72%. Light yellow solid; m.p. 192 °C; IR (KBr) cmÀ1: 3050,
2960, 2908, 1471,1458, 1259, 1202, 1109, 1036, 945, 885, 840, 885,
803, 750, 568, 552; 1H NMR (CDCl3, 600 MHz): d (ppm) = 6.07 (s,
2H, OCH2O), 7.25 (s, 1H, HAr), 7.33 (s, 1H, HAr), 7.59 (dt, 1H,
3
3JH–H = 6.0 Hz, HAr), 7.60 (d, 1H, JH–H = 6.0 Hz, HAr), 7.66 (dt,
3
3
1H, JH–H = 6.0 Hz, HAr), 7.72 (d, 1H, JH–H = 6.0 Hz, HAr), 7.84 (d,
3
C
12H10OS: 202.04524; Found: 202.04508; MS (EI, 70 eV) m/z (%)
202 [M+, 100], 96 [M+, –CHO, –C6H5, 14]; Anal. calcd for
12H10OS: C, 71.26; H, 4.98; S, 15.85; Found: C, 71.09; H, 5.14; S,
1H, JH–H = 12.0 Hz, HAr), 8.14 (s, 1H, HAr); 13C NMR (CDCl3,
150 MHz): d (ppm) = 101.00, 102.54, 103.23, 120.24, 122.50,
125.50, 126.21, 126.48, 126.89, 126.89, 127.51, 128.42, 129.41,
129.44, 130.19, 131.67, 147.84, 147.92; HRMS (EI, 70 eV): m/z
[M]+ calcd for C19H12O2: 272.08373; found: 272.08417; MS (EI,
70 eV) m/z (%) 272 [M+, 100]; Anal. Calcd for C19H12O2: C, 83.81;
H, 4.44; Found: C, 83.54; H, 4.67.
C
15.61.
2.3.9. 3-(3,4,5-Trimethoxybenzyl)thiophene-2-carboxaldehyde (3i)
Yield: 79%. White solid; m.p. 84 °C; 1H NMR (CDCl3, 600 MHz): d
(ppm) = 3.78 (s, 6H, 2xOCH3), 3.79 (s, 3H, OCH3), 4.24 (s, 2H, CH2),
3
6.37 (s, 2H, 2xHAr), 6.92 (d, 1H, JH–H = 6.0 Hz, HAr), 7.62 (d, 1H,
2.3.14. 1,3-Dimethoxyanhtracene (4d)
3JH–H = 6.0 Hz, HAr), 10.05 (s, 1H, CHO); 13C NMR (CDCl3,
150 MHz): d (ppm) = 34.54, 55.92, 55.92, 60.69, 105.46, 105.46,
131.20, 134.48,134.68, 136.49, 137.77, 149.63, 153.24, 153.24,
182.18; HRMS (EI, 70 eV): m/z [M]+ Calcd for C15H16O4S:
292.07693; Found: 292.07819; MS (EI, 70 eV) m/z (%) 292
[M+, 100], 261 [M+, -OMe, 20], 217 [M+, –CHO, -Me, -OMe, 18],
202 [M+, –CHO, -2xMe, -OMe, 10]; Anal. calcd for C15H16O4S: C,
61.63; H, 5.52; S, 10.97; Found: C, 61.51; H, 5.47; S, 10,69.
Yield: 91%. Yellow solid; m.p. 70 °C; IR (KBr) cmÀ1: 3046, 3023,
2997, 2964, 2936, 2902, 2826, 1636, 1627, 1570, 1546, 1450, 1418,
1369, 1345, 1312, 1279, 1247, 1201, 1153, 1136, 1093, 1043, 941,
886, 816, 735, 594, 529; 1H NMR (CDCl3, 200 MHz): d (ppm) = 3.96
(s, 3H, OCH3), 4.05 (s, 3H, OCH3), 6.46 (d, 1H, HAr), 6.82 (d, 1H, HAr),
4
3
7.41 (dt, 1H, JH–H = 5.0 Hz, JH–H = 10.0 Hz, HAr), 7.47 (dt, 1H,
3
3
4JH–H = 5.0 Hz, JH–H = 10.0 Hz, HAr), 7.93 (d, 1H, JH–H = 10.0 Hz,
4
H
Ar), 8.01 (d, 1H, JH–H = 5.0 Hz, HAr), 8.21 (s, 1H, HAr), 8.74 (s, 1H,
H
Ar); 13C NMR (CDCl3, 125 MHz): d (ppm) = 55.38, 55.70, 96.27,
2.3.10. 2-(Benzo[b]thien-2-ylmethyl)benzaldehyde (3j)
97.44, 121.26, 122.23, 123.78, 124.27, 125.86, 127.37, 128.90,
129.94, 132.69, 133.12, 156.68, 157.77; HRMS (EI, 70 eV): m/z
[M]+ Calcd for C16H14O2: 238.09938; Found: 238.09954; MS (EI,
70 eV) m/z (%) 238 [M+, 100], 223 [M+, -Me, 18]; Anal. Calcd for
Yield: 55%. Yellow oil; 1H NMR (CDCl3, 200 MHz):
d
(ppm) = 4.68 (s, 2H, CH2), 6.96 (s, 1H, HAr), 7.18–7.35 (m, 2H,
3
2xHAr), 7.36–7.67 (m, 4H, 4xHAr), 7.70–7.76 (d, 1H, JH–H = 8.0 Hz,
3
H
Ar), 7.82–7.88 (d, 1H, JH–H = 6.0 Hz, HAr) 10.24 (s, 1H, CHO); 13C
C16H14O2: C, 80.65; H, 5.92; Found: C, 80.49; H, 5.96.
NMR (CDCl3, 50 MHz): d (ppm) = 32.19, 120.79, 120.88, 121.80,
122.54, 122.96, 126.32, 130.15, 131.75, 132.47, 132.77, 138.46,
138.68, 140.14, 142.97, 191.14; HRMS (EI, 70 eV): m/z [M]+ Calcd
for C16H12OS: 252.06089; Found: 252.06021; MS (EI, 70 eV) m/z
(%) 252 [M+, 100], 234 [M+, –H2O, 58], 118 [M+, –C8H5S (benzothio-
phene), 62]. Anal. calcd for C16H12OS: C, 76.16; H, 4.79; S, 12.71;
Found: C, 76.14; H, 4.68; S, 12.83.
2.3.15. 1,2,3-Trimethoxyanhtracene (4e)
Yield: 72%. Light yellow solid; m.p. 86 °C; IR (KBr) cmÀ1: 3049,
3004, 2966, 2930, 2831, 1627, 1565, 1540, 1471, 1462, 1450, 1421,
1355, 1311, 1285, 1236, 1204, 1133, 1092, 1031, 1000, 941, 913,
888, 751, 601; 1H NMR (CDCl3, 200 MHz): d (ppm) = 4.00 (s, 3H,
OCH3), 4.02 (s, 3H, OCH3), 4.13 (s, 3H, OCH3), 7.02 (s, 1H, HAr),