Hydrochloric Acid → HCID 22906507, compound

HRID 1488780Notes

Reaction equation

HRID 1488780 reaction equation
[OH:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH:15]([CH3:17])[CH3:16])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:29])[CH:5]=[C:6](OC1C=CC(OC(C)C)=CC=1)[O:7]2.[OH:30][C:31]1[CH:36]=[CH:35][C:34]([SH:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[OH:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH:15]([CH3:16])[CH3:17])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:29])[CH:5]=[C:6]([S:37][C:34]1[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=1)[O:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 15288782HCID 15288782, compound

Product 1

HCID 22906507HCID 22906507, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture consisting of 9.49 g of 5-hydroxy-7-isopropoxy-2-(4-isopropoxyphenoxy)-6-methoxychromone obtained in Example 4, 4.49 g of 4-hydroxythiophenol, 4.91 g of potassium carbonate, and 200 ml of acetone was stirred over 1.2 hours at room temperature. The solution thus reacted was made weakly acidic by addition of dilute hydrochloric acid. The product was extracted twice with chloroform. The organic layer was washed with saturated salt water and was then dried over sodium sulfate anhydride. The solvent was distilled out under reduced pressure. The resulting crude product was recrystallized from hexane:ethyl acetate, so that 7.95 g of 5-hydroxy-2-(4-hydroxyphenylthio)-7-isopropoxy-6-methoxychromone with the following physicochemical properties was obtained.

Workup

  1. customThe solution thus reacted
  2. extractionThe product was extracted twice with chloroform
  3. washThe organic layer was washed with saturated salt water
  4. dry with materialwas then dried over sodium sulfate anhydride
  5. distillationThe solvent was distilled out under reduced pressure
  6. customThe resulting crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-3747366b95704a96aa3f1ea623eff59a
Source dataset
uspto-grants-1997_10
Patent number
US05675023

Reaction notes

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