Reaktion #530076

Reaktionsgleichung

Orcinol monohydrate

2-trifluoromethylbenzenesulfonyl chloride

→

title compound

Ausbeute 55.0%

5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol

Ausbeute 55.0%

Lösungsmittel

diethyl ether

NaHCO3

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted into ethyl acetate (3×80 mL)
2. 2
   WaschenThe organic phase was washed with brine (2×50 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   SonstigeAfter removing the solvent in vacuo
5. 5
   Sonstigethe residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane)

Vorschrift

Orcinol monohydrate (2.84 g, 20.0 mmol) and 2-trifluoromethylbenzenesulfonyl chloride (4.90 g, 20.0 mmol) were mixed in saturated aqueous NaHCO3 (70 mL) and diethyl ether (70 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (100 mL) and extracted into ethyl acetate (3×80 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 2% ethyl acetate in dichloromethane) to give the title compound as a white solid (3.65 g, 55%). 1H-NMR (300 MHz, CDCl3) δ 8.12 (d, J=8.0 Hz, 1 H), 7.98 (d, J=7.9 Hz, 1 H), 7.80 (t, J=8.2 Hz, 1 H), 7.69 (t, J=7.8 Hz, 1 H), 6.55 (s, 1 H), 6.48 (s, 1 H), 6.39 (s, 1 H), 5.11 (s, 1 H), 2.23 (s, 3 H).

Quelle