Reaktionsgleichung
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19]>C([O-])(O)=O.[Na+].C(OCC)C>[OH:5][C:4]1[CH:3]=[C:2]([O:10][S:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])(=[O:20])=[O:19])[CH:9]=[C:7]([CH3:8])[CH:6]=1Komponenten
Versuchsvorschrift
Orcinol monohydrate (1.42 g, 10 mmol) and 2-chlorobenzenesulfonyl chloride (2.43 g, 11 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature for 2 days. The reaction mixture was quenched with 50 mL of water and extracted into ethyl acetate (3×50 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 (2% ethyl acetate in methylene chloride) to give the title compound as a pale-yellow liquid (2.15 g, 71%). 1H-NMR (300 MHz, CDCl3) δ 2.22 (s, 3 H), 5.24 (s, 1 H), 6.43 (s, 1 H), 6.52 (s, 2H), 7.38 (m, 1 H), 7.60 (m, 2 H), and 7.96 (dd, 1 H, J=0.6, 3.9 Hz).
Aufarbeitung
- customThe reaction mixture was quenched with 50 mL of water
- extractionextracted into ethyl acetate (3×50 mL)
- washThe organic phase was washed with brine (2×50 mL)
- dry with materialdried over Na2SO4
- customAfter removing the solvent in vacuo
- customthe residue was purified by flash column chromatography (2% ethyl acetate in methylene chloride)
Quellen und Nachweise
- ORD-Eintrag
- ord-1f2fd93d7598488eae2c760e1264d5bd
- Quelldatensatz
- uspto-grants-2000_10
- Patentnummer
- US06133315
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