Hydrochloric Acid → 2-(4-Hydroxyphenylthio)-7-isopropoxy-5-methoxychromone

HRID 441061Notes

Reaction equation

HRID 441061 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:18])[CH:10]=[C:11]([S:15]([CH3:17])=O)[O:12]2)=[C:7]([O:19][CH3:20])[CH:6]=1)([CH3:3])[CH3:2].[OH:21][C:22]1[CH:27]=[CH:26]C(S)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[OH:21][C:22]1[CH:27]=[CH:26][C:17]([S:15][C:11]2[O:12][C:13]3[C:8]([C:9](=[O:18])[CH:10]=2)=[C:7]([O:19][CH3:20])[CH:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:14]=3)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 229064677-Isopropoxy-5-methoxy-2-methylsulfinylchromone

Product 1

HCID 229064892-(4-Hydroxyphenylthio)-7-isopropoxy-5-methoxychromoneYield 57.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 146 mg of 7-isopropoxy-5-methoxy-2-methylsulfinylchromone (0.493 mmol ) , 93 mg of 4-hydroxybenzenethiol(0.740 mmol), 102 mg of potassium carbonate (0.740 mmol) and 6 ml acetone was stirred for 2 hours at room temperature. The reaction solution was neutralized with dilute hydrochloric acid and extracted twice with ethyl acetate, and the organic layer was washed with saturated NaCl water and was then dried over sodium sulfate anhydride. The solvent was distilled off under reduced pressure, and the crude product was subjected to recrystallization from acetone-methanol, to give 102 mg of 2-(4-hydroxyphenylthio)-7-isopropoxy-5-methoxychromone (57% yield).

Workup

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

Sources & evidence

ORD record
ord-b75679b73f6449178d2300d616707cb5
Source dataset
uspto-grants-1996_05
Patent number
US05521216

Reaction notes

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