Sodium Iodide → HCID 56973356, compound

HRID 1878308Notes

Reaction equation

HRID 1878308 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>C1COCC1.O>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[C:3]=1[C:10](=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 697091-(2-Hydroxy-6-methoxyphenyl)ethan-1-oneHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 56973356HCID 56973356, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A flask is charged with 1-(2-hydroxy-6-methoxyphenyl)ethanone (30 g, 180.5 mmol), potassium carbonate, (49.9 g, 361 mmol), sodium iodide (2.68 g, 18.1 mmol), and 4-methoxybenzylchloride (27.0 mL, 198.6 mmol) in THF and the mixture is heated to reflux overnight. The mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with brine and dried over anhydrous MgSO4, filtered, and concentrated. The crude product is purified by silica gel chromatography with an eluent of ethyl acetate/hexanes to give 32.51 g (57%) of the desired product as a white solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel chromatography with an eluent of ethyl acetate/hexanes

Sources & evidence

ORD record
ord-466296c266ee464ebc9131991ca6cd6f
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

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