2-Chlorobenzenesulfonyl chloride → 3-(2-Chlorophenylsulfonyloxy)-5-methylphenol

HRID 651511

Reaktionsgleichung

Reaktionsgleichung von HRID 651511
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]=1

Komponenten

5

Edukt 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Produkt 1

HCID 112779473-(2-Chlorophenylsulfonyloxy)-5-methylphenolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

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 (20% ethyl acetate in methylene chloride) to give the title compound as a pale-yellow liquid (2.15 g, 71%).

Aufarbeitung

  1. customThe reaction mixture was quenched with 50 mL of water
  2. extractionextracted into ethyl acetate
  3. washThe organic phase was washed with brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (20% ethyl acetate in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-e568463a56ef4852ac4c744b059ad156
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281206B1

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