Isopropyl iodide → HCID 21466179, compound

HRID 2078447Notes

Reaction equation

HRID 2078447 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.I[CH:17]([CH3:19])[CH3:18].[OH-].[K+]>C(O)C.O>[CH:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:3][CH:4]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 160694,4'-Dihydroxydiphenyl ether

Product 1

HCID 21466179HCID 21466179, compoundYield 443.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4,4′-oxydiphenol (3.680 g, 1.82 mmol) and 2-iodopropane (1.82 mL, 1.82 mmol) in ethanol (8.0 mL) at refluxing was added KOH (88%, 1.22 g, 1.91 mmol, 1.05 equivalents) in water (4.0 mL) over a period of 10 min. The resulting mixture was refluxed for 1 hour. Ethanol was removed. The residue was dissolved in ether, which was washed with brine (1×), dried over MgSO4 and concentrated. The residue was purified on a silica gel column eluting with ethyl acetate and hexane gradient to give the title product as a white solid (1.970 g, 44%)

Workup

  1. temperatureat refluxing
  2. temperatureThe resulting mixture was refluxed for 1 hour
  3. customEthanol was removed
  4. dissolutionThe residue was dissolved in ether
  5. washwhich was washed with brine (1×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified on a silica gel column
  9. washeluting with ethyl acetate and hexane gradient

Sources & evidence

ORD record
ord-30e64588dd074058a02e255f60ff7cef
Source dataset
uspto-grants-2011_04
Patent number
US07928243B2

Reaction notes

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