Hydrochloric Acid → 5,7-Dihydroxy-2-(4-hydroxyphenylthio)chromone

HRID 1779522Notes

Reaction equation

HRID 1779522 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([S:13]([CH3:15])=O)[O:7]2.[OH:17][C:18]1[CH:23]=[CH:22]C(S)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([S:13][C:15]1[CH:22]=[CH:23][C:18]([OH:17])=[CH:19][CH:20]=1)[O:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 229064885,7-Dihydroxy-2-methylsulfinylchromone

Product 1

HCID 229064625,7-Dihydroxy-2-(4-hydroxyphenylthio)chromoneYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture consisting of 32 mg (0.134 mmol) 5,7-dihydroxy-2-methylsulfinylchromone, 20 mg (0.161 mmol) 4-hydroxybenzenethiol, 41 mg (0.295 mmol) potassium carbonate, and 2 ml acetone was stirred overnight at room temperature. The solution thus reacted was neutralized by addition of dilute hydrochloric acid. Subsequently, the product was extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled out under reduced pressure. The resulting crude product was subjected to recrystallization from acetone-hexane, whereby 14.6 mg of 5,7-dihydroxy-2-(4-hydroxyphenylthio)chromone was obtained (yield: 36%).

Workup

  1. customThe solution thus reacted
  2. extractionSubsequently, the product was extracted twice with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled out under reduced pressure
  6. customThe resulting crude product was subjected to recrystallization from acetone-hexane

Sources & evidence

ORD record
ord-7eb4cd162ba74148a6d3aeeb79ea4d90
Source dataset
uspto-grants-1997_05
Patent number
US05627204

Reaction notes

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