Thioglycolic Acid → (4,5-Dihydroxy-10-oxo-9,10-dihydro-anthracen-9-ylsulfanyl)-acetic acid

HRID 1651144Notes

Reaction equation

HRID 1651144 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][C:21]([OH:23])=[O:22]>ClCCl>[C: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)([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 27650410-Bromo-1,8-dihydroxy-10H-anthracen-9-one

Product 1

HCID 20067256(4,5-Dihydroxy-10-oxo-9,10-dihydro-anthracen-9-ylsulfanyl)-acetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-Bromo-1,8-dihydroxy-9-anthrone (305 mg) was dissolved in dichloromethane (10 ml) and mercaptoacetic acid (0.07 ml) was added. The solution was stirred at room temperature for 3 days, during which time a yellow precipitate was formed, which was filtered off and recrystallised from absolute ethanol to give 10-(carboxymethylthio)-1,8-dihydroxy-9-anthrone (237 mg, 75%) as yellow needles, melting point 151°-152° C. (Found: C 60.9, H 3.8, S 10.1%; M=316.0410; C16H12O5S requires C 60.75, H3.8, S 10.1%, M=316.0405).

Workup

  1. customwas formed
  2. filtrationwhich was filtered off
  3. customrecrystallised from absolute ethanol

Sources & evidence

ORD record
ord-cadb5125807f4fd4a30b61751d33355e
Source dataset
uspto-grants-1990_05
Patent number
US04927845

Reaction notes

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