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General Experimental Procedure: To a mixture of a phenol (1 mmol) and aromatic aldehyde (1 mmol) in MeCN or acrylonitrile (5 mL), triflic acid (10 mol%) was added. The mixture was heated under reflux and the reaction was monitored by TLC. After completion of the reaction, H2O (10 mL) was added and the mixture was extracted with EtOAc (3 × 10 mL). The extract was dried and concentrated. The residue was subjected to column chromatography (silica gel; eluent: hexane-EtOAc, 4:1) to obtain the pure amido-alkyl phenol.
The spectral (IR, 1H and 13C NMR and MS) data of some representative products are given below.
Compound 4a: IR (KBr): 3422, 1654, 1511, 1460, 1376, 1269 cm-1. 1H NMR (200 MHz, CDCl3 + DMSO-d
6): δ = 8.99 (br s, 1 H), 8.01 (m, 1 H), 7.90 (br s, 1 H), 7.44-7.52 (m, 2 H), 6.84 (d, J = 8.0 Hz, 3 H), 6.68 (d, J = 8.0 Hz, 3 H), 1.92 (s, 3 H). 13C NMR (50 MHz, DMSO-d
6): δ = 23.0, 55.4, 115.8, 121.8, 122.3, 129.3, 130.4, 132.2, 134.4, 146.1, 148.2, 157.1, 169.3. MS (FAB): m/z (%) = 278 (2), 276 (6) [M + H]+·, 184 (33), 182 (100).
Compound 4i: IR (KBr): 3409, 1644, 1537, 1370, 1330, 1272 cm-1. 1H NMR (200 MHz, CDCl3 + DMSO-d
6): δ = 9.82 (br s, 1 H), 8.26 (m, 1 H), 8.02 (m, 1 H), 6.62-7.76 (m, 6 H), 7.32-7.41 (m, 3 H), 7.18-7.25 (m, 4 H), 2.06 (s, 3 H). 13C NMR (50 MHz, DMSO-d
6): δ = 22.9, 48.0, 118.4, 119.1, 122.5, 123.3, 123.4, 123.9, 125.1, 125.3, 126.4, 126.7, 127.2, 127.9, 128.7, 128.8, 128.9, 131.3, 132.2, 132.9, 140.6, 153.2, 169.1. MS (FAB): m/z (%) = 342 (2) [M + H]+·, 198 (100).
Compound 4k: IR (KBr): 3425, 1647, 1513, 1462, 1274 cm-1. 1H NMR (200 MHz, CDCl3 + DMSO-d
6): δ = 9.65 (br s, 1 H), 9.12 (d, J = 8.0 Hz, 1 H), 8.00 (m, 1 H), 7.68 (d, J = 8.0 Hz, 1 H), 7.62 (d, J = 8.0 Hz, 1 H), 7.36 (m, 1 H), 7.06-7.22 (m, 5 H), 6.64 (d, J = 8.0 Hz, 2 H), 3.64 (s, 3 H), 2.02 (s, 3 H). 13C NMR (50 MHz, DMSO-d
6): δ = 23.2, 48.2, 55.5, 113.9, 119.0, 119.5, 122.9, 126.8, 127.8, 129.0, 129.6, 132.8, 134.9, 153.6, 158.2, 169.6. MS (FAB): m/z (%) = 322 (3) [M + H]+·, 178 (100).
Compound 4m: IR (KBr): 3446, 1657, 1622, 1514, 1337, 1276 cm-1. 1H NMR (200 MHz, CDCl3 + DMSO-d
6): δ = 9.61 (br s, 1 H), 8.22 (m, 1 H), 8.00 (m, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 7.66 (d, J = 8.0 Hz, 1 H), 7.41 (m, 1 H), 7.10-7.28 (m, 7 H), 6.21-6.38 (m, 2 H), 5.61 (m, 1 H). 13C NMR (50 MHz, DMSO-d
6): δ = 47.5, 117.5, 118.0, 121.8, 122.2, 125.0, 125.8, 127.0, 127.2, 127.5, 128.5, 128.7, 130.6, 130.9, 131.9, 140.1, 152.4, 164.0. MS (FAB): m/z (%) = 340 (2), 338 (6) [M + H]+·, 196 (33), 194 (100).
