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

HRID 358839Notes

Reaction equation

HRID 358839 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5ea85ebd568e4a86b1a578bb82a32bf7
Source dataset
uspto-grants-1991_03
Patent number
US04997961

Reaction notes

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