反应详情

Vanillic acid (C1) (114.5 g, 0.68 mol) was dissolved in a solution of sodium hydroxide (54.5 g, 1.36 mol) in water (400 mL). 3-Bromopropan-1-ol (101.3 g, 0.73 mol, 1.07 eq) was added and the mixture was heated under reflux for 5 hours. The mixture was cooled and acidified with 2.5 M HCl. The resulting precipitate was filtered and dried under vacuum. Recrystallisation from butan-2-one gave the product as an off white solid. (110 g, 71%). mp: 162° C.; 1H NMR (DMSO-d6, 400 MHz) δ 7.56 (dd, 1H, J=1.98 Hz, J=8.39 Hz), 7.44 (d, 1H, J=1.96 Hz), 7.04 (d, 1H, J=8.50 Hz), 4.55 (bs, 1H), 4.09 (t, 2H, J=6.37 Hz), 3.80 (s, 3H, OMe), 3.57 (t, 2H, J=6.20 Hz), 1.88 (p, 2H, J=6.29 Hz); 13C NMR (100 MHz, DMSO-d6) δ167.1, 152.0, 123.1, 122.7, 112.0, 111.7, 65.3, 57.2, 55.4, 31.9; IR (CHCl3) 1673, 1596, 1585, 1517, 1425, 1271, 1227, 1188, 1134, 1051, 1026, 951, 876, 814, 758 cm−1; MS (ES−) m/z (relative intensity) 225.04 ([M−H]−, 100).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 5 hours
3. temperatureThe mixture was cooled
4. filtrationThe resulting precipitate was filtered
5. customdried under vacuum
6. customRecrystallisation from butan-2-one
7. customgave the product as an off white solid