반응 #161149

반응 방정식

urea

H2SO4 H2O

NaNO2

NaNO2

H2SO4 H2O

2-tert-butyl-5-nitroaniline

→

2-tert-butyl-5-nitrophenol

수율 62.0%

용매

water

H2SO4

반응 조건

후처리

1. 1
   온도the mixture was refluxed for 5 min
2. 2
   온도while heating
3. 3
   온도at reflux
4. 4
   온도The reaction mixture was cooled to room temperature
5. 5
   추출extracted with EtOAc twice
6. 6
   세척The combined organic layers were washed with brine
7. 7
   건조dried over MgSO4
8. 8
   기타After removal of solvent
9. 9
   기타the residue was purified by column chromatography (0-10% EtOAc-Hexane)

실험 절차

To a mixture of 2-tert-butyl-5-nitroaniline (1.94 g, 10 mmol) in 40 mL of 15% H2SO4 was added dropwise a solution of NaNO2 (763 mg, 11.0 mmol) in water (3 mL) at 0° C. The resulting mixture was stirred at 0-5° C. for 5 min. Excess NaNO2 was neutralized with urea, then 5 mL of H2SO4—H2O (v/v 1:2) was added and the mixture was refluxed for 5 min. Three additional 5 mL aliquots of H2SO4—H2O (v/v 1:2) were added while heating at reflux. The reaction mixture was cooled to room temperature and extracted with EtOAc twice. The combined organic layers were washed with brine and dried over MgSO4. After removal of solvent, the residue was purified by column chromatography (0-10% EtOAc-Hexane) to give 2-tert-butyl-5-nitrophenol (C-1-a) (1.2 g, 62%). 1H NMR (400 MHz, CDCl3) δ 7.76 (dd, J=8.6, 2.2 Hz, 1H), 7.58 (d, J=2.1 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 5.41 (s, 1H), 1.45 (s, 9H); HPLC ret. time 3.46 min, 10-99% CH3CN, 5 min run.

출처