2-Mercaptoethanol → 1,8-Dihydroxy-10-(2-hydroxy-ethylsulfanyl)-10H-anthracen-9-one

HRID 1651147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651147
Br[CH:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[C:8]2[C:7]([OH:18])=[CH:6][CH:5]=[CH:4][C:3]1=2.[SH:19][CH2:20][CH2:21][OH:22]>ClCCl>[OH:22][CH2:21][CH2:20][S:19][CH:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[C:8]2[C:7]([OH:18])=[CH:6][CH:5]=[CH:4][C:3]1=2

Komponenten

4

Edukt 2

HCID 15672-MercaptoethanolHCID 27650410-Bromo-1,8-dihydroxy-10H-anthracen-9-one

Produkt 1

HCID 200672591,8-Dihydroxy-10-(2-hydroxy-ethylsulfanyl)-10H-anthracen-9-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10-Bromo-1,8-dihydroxy-9-anthrone (100 mg) was dissolved in dichloromethane (7 ml) and 2-mercaptoethanol (0.03 ml) was added. The solution was stirred at room temperature for 7 hours, during which time the light brown solution became pale green. Removal of the solvent and recrystallisation of the residue from a hexane/chloroform mixture (5:1) gave 10-(2-hydroxyethylthio)-1,8-dihydroxy-9-anthrone (89 mg, 90%) as pale yellow needles, melting point 146°-147° C. (Found: C 63.1, H 4.75, S 10.7; C16H14O4S requires C 63.55, H 4.7, S 10.6%).

Aufarbeitung

  1. customRemoval of the solvent and recrystallisation of the residue from a hexane/chloroform mixture (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-1e83ca58b55e4aa99edb960b25a4b399
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927845

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