Sodium Iodide → HCID 28369310, compound

HRID 1696706Notes

Reaction equation

HRID 1696706 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CC(=O)CC.O>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62714'-HydroxypropiophenoneHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 28369310HCID 28369310, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

4′-Hydroxypropiophenone (50.0 g, 0.33 mol), potassium carbonate (69.0 g, 0.50 mol), and sodium iodide (25.0 g, 0.17 mol) were suspended in 2-butanone (500 mL), and with stirring at room temperature, 4-methoxybenzyl chloride (57.4 g, 0.37 mol) was added at room temperature. The reaction solution was stirred at 60° C. for 12 hours. The reaction solution was poured into water, extracted with ethyl acetate, the organic layer was washed with saturated saline, and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting pale yellow solid was washed with hexane to obtain the entitled compound (86.3 g, 96%) as a milky white solid.

Workup

  1. stirringThe reaction solution was stirred at 60° C. for 12 hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated saline
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe resulting pale yellow solid was washed with hexane

Sources & evidence

ORD record
ord-0baeab38e5974d85886f3dfbdd2092cb
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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