o-Toluenesulfonyl chloride, 5-nitro- → 5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenol

HRID 442947

Reaktionsgleichung

Reaktionsgleichung von HRID 442947
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[S:21](Cl)(=[O:23])=[O:22]>C([O-])(O)=O.[Na+].C(OCC)C.O>[CH3:8][C:7]1[CH:9]=[C:2]([O:10][S:21]([C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[CH3:11])(=[O:22])=[O:23])[CH:3]=[C:4]([OH:5])[CH:6]=1

Komponenten

6

Edukt 2

HCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 3083941Resorcinol, 5-methyl-, monohydrate

Produkt 1

HCID 544160485-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Orcinol monohydrate (2.84 g, 20.0 mmol) and 2-methyl-5-nitrobenzenesulfonyl chloride (4.71 g, 20.0 mmol) were mixed in saturated aqueous NaHCO3 (60 mL) and diethyl ether (60 mL). The biphasic mixture was stirred vigorously at ambient temperature overnight. The reaction mixture was diluted with water (100 mL) and extracted into ethyl acetate (3×60 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 5% ethyl acetate in dichloromethane) to give the title compound as a pale yellow solid (4.20 g, 72%). 1H-NMR (300 MHz, CDCl3) δ 8.71 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 6.56 (s, 1H), 6.44 (s, 1H), 6.33 (s, 1H), 5.42 (s, 1H), 2.91 (s, 3H), 2.23 (s, 3H).

Aufarbeitung

  1. extractionextracted into ethyl acetate (3×60 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-aee23faa0033478fbc7fd956f6c5f270
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

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