HCID 66650188, compound → HCID 11528963, compound

HRID 418820Notes

Reaction equation

HRID 418820 reaction equation
CO[C:3]1[C:8]([O:9]C)=[CH:7][CH:6]=[CH:5][C:4]=1[C:11](=[O:23])[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=1)=[O:14]>I.CC(O)=O.O>[OH:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[O:14][C:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[CH:12][C:11]2=[O:23]

Participants

5

Reactant 1

HCID 66650188HCID 66650188, compound

Product 1

HCID 11528963HCID 11528963, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 24841Hydrogen iodideSolvent

Conditions

Temperature
110 °C

Procedure

1-(2,3-Dimethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione (3.1 g, 9.86 mmol) was dissolved in mixture of HI (10 mL) and AcOH (10 mL) and heated at 110° C. for 4 days. The reaction mixture was cooled to rt, diluted with water and solids were filtered. The solid product was washed with water, dried and purified by column chromatography, using 30% EtOAc in dichloromethane to give 1.3 g (52%) of 8-hydroxy-2-(4-hydroxy-phenyl)-4H-chromen-4-one. MS (ES) m/z: 255.08 (M+1), and 154.15.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationwere filtered
  3. washThe solid product was washed with water
  4. customdried
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-083ea547c4ba4e439fe2f3d6e54c52a7
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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