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

HRID 441056Notes

Reaction equation

HRID 441056 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 of 32 mg of 5,7-dihydroxy-2-methylsulfinylchromone (0.134 mmol), 20 mg of 4-hydroxybenzenethiol (0.161 mmol), 41 mg of potassium carbonate (0. 295 mmol) and 2 ml acetone was stirred overnight at room temperature. The reaction solution was neutralized with dilute hydrochloric acid and then extracted twice with ethyl acetate. The organic layer was washed with saturated NaCl water and dried over sodium sulfate anhydride. The solvent was distilled off under reduced pressure, and the crude product was subjected to recrystallization from acetone-hexane, to give 14.6 mg of 5,7-dihydroxy-2-(4-hydroxyphenylthio)chromone (36% yield).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated NaCl water
  3. dry with materialdried over sodium sulfate anhydride
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe crude product was subjected to recrystallization from acetone-hexane

Sources & evidence

ORD record
ord-0d726f084be9443a8d4285eff3c513d6
Source dataset
uspto-grants-1996_05
Patent number
US05521216

Reaction notes

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