Quinone → 2-(4-Fluorobenzenesulfonyl)benzene-1,4-diol

HRID 584021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584021
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([OH:18])=[O:17])=[CH:12][CH:11]=1>CCO.O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([C:6]2[CH:5]=[C:4]([OH:7])[CH:3]=[CH:2][C:1]=2[OH:8])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 4650QuinoneHCID 421250Sodium 4-fluorobenzene sulfinate

Produkt 1

HCID 223448682-(4-Fluorobenzenesulfonyl)benzene-1,4-diolAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of benzoquinone (23.5 g, 217 mmol) in 500 ml EtOH was added at RT over 30 min to a solution of 4-fluoro-benzenesulfinic acid (34.8 g, 217 mmol) in EtOH (300 mL) and water (500 mL). The resulting solution was stirred 2 h at RT, then diluted to 4 l with warm water. The solution was cooled to 4° C. for 62 h and crystals formed. The crystalline solid was collected by suction filtration and washed with water (3×500 mlL and hexanes (2×500 mL) and dried to give the title compound of Step B (40.8 g). MS (APCl−) Calc.: 268.0. Found: 267.1 (M−1).

Aufarbeitung

  1. temperatureThe solution was cooled to 4° C. for 62 h
  2. customcrystals formed
  3. filtrationThe crystalline solid was collected by suction filtration
  4. washwashed with water (3×500 mlL and hexanes (2×500 mL)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9f37e7aa31cb481caf056ef20b9ca7b0
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924310B2

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