반응 #470595

반응 방정식

4-Fluorophenol

1-methylcyclohexanol

sulfuric acid

→

4-fluoro-2-(1-methylcyclohexyl)phenol

용매

CH2Cl2

반응 조건

후처리

1. 1
   추출The reaction mixture was then extracted by CH2Cl2 (250 mLx3)
2. 2
   세척The organic layer was washed with saturated a.q NaHCO3
3. 3
   건조, dried over MgSO4
4. 4
   기타evaporated under vacuum
5. 5
   기타The residue was purified by column chromatography on silica gel

실험 절차

4-Fluorophenol (41.8 g, 373 mmol) and 1-methylcyclohexanol (63.8 g, 560 mmol) dissolved in 600 mL of dried CH2Cl2, were treated with concentrated sulfuric acid (98%, 22.3 mL, 418 mmol). The mixture was stirred at room temperature for 50 hours. The reaction mixture was then extracted by CH2Cl2 (250 mLx3). The organic layer was washed with saturated a.q NaHCO3., dried over MgSO4, and evaporated under vacuum. The residue was purified by column chromatography on silica gel to give 4-fluoro-2-(1-methylcyclohexyl)phenol as a dark green oil—47.6 g. 1H NMR (400 MHz, CDCl3) δ 7.00 (dd, J=3.2, 11.2 Hz, 1H), 6.76-6.71 (m, 1H), 6.62-6.59 (m, 1H), 5.27 (brs, 1H), 2.13-2.07 (M, 2H), 1.70-1.37 (m, 8H), 1.32 (s, 3H).

출처