反应详情

65% HNO3 (80 ml) was stirred at −5° C.±1° C. and 98% H2SO4 (10 mix 10) was added dropwise. To the stirring solution of HNO3/H2SO4 was added 3-chloroacetophenone (54) (12.0 g, 77.6 mmol). The mixture was stirred at −5□±1□ for 3 h and poured into crushed ice, and extracted with CH2Cl2. The extract was dried over MgSO4 and evaporated. The crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1) to give 55 as yellow solid (9.3 g, 46.6 mmol). Yield: 55.8%; mp 47-49° C.; 1H-NMR (CDCl3, 200 MHz): δ 2.48 (s, 3H), 7.32 (d, J=2.4 Hz, 1H), 7.49 (dd, J=8.8, 2.2 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 198.27, 143.78, 141.05, 139.44, 130.55, 127.36, 125.91, 30.06; Anal. Calcd for C8H6ClNO3: C, 48.14; H, 3.03; N, 7.02.

1. additionpoured
2. custominto crushed ice
3. extractionextracted with CH2Cl2
4. dry with materialThe extract was dried over MgSO4
5. customevaporated
6. customThe crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1)