Potassium Iodide → HCID 23113981, compound

HRID 2376324Notes

Reaction equation

HRID 2376324 reaction equation
[CH:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][C:28](=[O:30])[CH3:29].[I-].[K+]>CC(C)=O.O>[CH:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[O:17][CH2:27][C:28]([CH3:29])=[O:30])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 23114251HCID 23114251, compound

Product 1

HCID 23113981HCID 23113981, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixed solution of 2-(4-isopropylbenzyl)-3,5-dimethylphenol obtained in Reference Example 148 (1.0 g, 3.93 mmol), potassium carbonate (1.30 g, 9.44 mmol), chloroacetone (436 mg, 4.72 mmol) and potassium iodide (100 mg) in acetone (15 mL) was heated under reflux for 16 hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The combined organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 888 mg (yield 73%) of the title compound. Oily matter.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe combined organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-4d88a29a91484e6c80a7619f716e8f9a
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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