Water → 3-(3-Chlorophenylsulfonyloxy)-5-methylphenol

HRID 1976084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976084
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:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.O>C([O-])(O)=O.[Na+].C(OCC)C>[OH:5][C:4]1[CH:3]=[C:2]([O:10][S:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([Cl:11])[CH:13]=2)(=[O:20])=[O:19])[CH:9]=[C:7]([CH3:8])[CH:6]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 179093-Chlorobenzenesulphonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Produkt 1

HCID 540176793-(3-Chlorophenylsulfonyloxy)-5-methylphenolAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Orcinol monohydrate (1.42 g, 10 mmol) and 3-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. After adding water (50 mL) to the mixture, the mixture was extracted with ethyl acetate (3×50 mL). The organic phase was then washed with brine (2×50 mL) and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (2% ethyl acetate in methylene chloride) to give the title compound as a pale-yellow liquid (2.08 g, 69%). 1H-NMR (300 MHz, CDCl3) δ 2.24 (s, 3 H), 5.32 (s, 1 H), 6.33 (t, 1 H, J=2.2 Hz), 6.40 (s, 1 H), 6.57 (s, 1 H), 7.48 (t, 1 H, J=8.0 Hz), 7.65 (m, 1 H), 7.73 (m, 1 H), and 7.86 (t, 1 H, J=1.8 Hz).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe organic phase was then washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash column chromatography (2% ethyl acetate in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-949db8a2fe6044a3b5eda261ae8b4b2b
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225302B1

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