Methyl iodide → 9H-Xanthen-9-one, 1,5-dimethoxy-3-(2-propenyloxy)-

HRID 585780Notes

Reaction equation

HRID 585780 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=[C:8]([O:19][CH2:20][CH:21]=[CH2:22])[CH:9]=[C:10]([OH:18])[C:11]=1[C:12]2=[O:17].[C:23](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=[C:8]([O:19][CH2:20][CH:21]=[CH2:22])[CH:9]=[C:10]([O:18][CH3:23])[C:11]=1[C:12]2=[O:17]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 11403772HCID 11403772, compound

Product 1

HCID 121783329H-Xanthen-9-one, 1,5-dimethoxy-3-(2-propenyloxy)-Yield 77%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of xanthone 2 (150 g, 0.5 mol) in dry DMF (500 mL) was added potassium carbonate (100 g, 0.72 mol) and methyl iodide (180 g, 1.28 mol) and the mixture was heated with constant stirring under argon to 80° C. for 1 hour. The mixture was allowed to cool to room temperature and diluted with 2L ethyl acetate and the remaining potassium carbonate was dissolved in dilute sulfuric acid. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford the xanthone 3 (120 g, 0.38 mol, 77%) as a pale yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool to room temperature
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c61f92dbbb224209b02f6fae0cdfaf95
Source dataset
uspto-grants-2005_08
Patent number
US06933396B2

Reaction notes

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