2-Iodophenol → HCID 24741349, compound

HRID 1027132Notes

Reaction equation

HRID 1027132 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]>CC(C)=O>[I:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:8][C:5]1[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 24741349HCID 24741349, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Picolyl chloride hydrochloride (4.00 g, 24.4 mmol) was dissolved in acetone (55 mL), potassium carbonate (10.1 g, 73.2 mmol) and o-iodophenol (6.97 g, 31.7 mmol) were added, and the mixture was heated under reflux for 24 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the obtained crystals, and the mixture was suction-filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound (4.02 g, 53%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  4. additionwas added to the obtained crystals
  5. filtrationthe mixture was suction-filtered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-0c744f609de74832bf7332022dd2ba00
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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