Hydrochloric Acid → Ethyl (2,4-dinitronaphthalen-1-yl)acetate
反応式
Cl.[N+:2]([C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:18](C(OCC)=O)[C:19]([O:21][C:22](C)(C)[CH3:23])=[O:20])([O-:4])=[O:3]>CCOC(C)=O>[N+:2]([C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([O-:4])=[O:3]参加物
4
実験手順
Concentrated HCl (1.5 mL) was added to a solution of t-butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate (0.60 g, 1.48 mmol) in AcOEt (6 mL), and the mixture was stirred overnight. The mixture was diluted with AcOEt (30 mL), washed with H2O (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Recrystallization (Ether) afforded ethyl (2,4-dinitronaphthalen-1-yl)acetate (0.31 g, 69%) as a pale orange solid. M.p. 132-134° C.; 1H NMR (CDCl3, 500 MHz) δ 8.71 (s, 1H), 8.61 (d, 8.5, 1H), 8.30 (d, 8.5, 1H), 7.92 (dt, 1.0, 8.5, 1H), 7.86 (dt, 1.5, 8.5, 1H), 4.51 (s, 2H), 4.22 (q, 7.5, 2H), 1.27 (t, 7.5, 3H); 304 (M−); IR (neat) 3087, 2989, 1732, 1528, 1422, 1355, 1204, 1169, 1027, 889, 832, 779 cm−1. FABMS (NBA) m/z 305 (M+H+).