تفاعل #491776

معادلة التفاعل

4-Fluorophenol

1-methylcyclohexanol

sulfuric acid

→

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

المردود 61.3%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe reaction mixture was then extracted by CH2C2 (250 mL×3)
2. 2
   غسيلThe organic layer was washed with saturated a.q NaHCO3
3. 3
   تجفيفdried over MgSO4
4. 4
   أخرىevaporated under vacuum
5. 5
   أخرىThe residue was purified by column chromatography on silica gel

الإجراء التجريبي

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 CH2C2 (250 mL×3). 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).

المصدر