Isopropyl iodide → HCID 21466179, compound

HRID 222646Notes

Reaction equation

HRID 222646 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 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4,4′-Oxydiphenol (3.68 g, 0.018 mmoL) and 2-iodopropane (1.82 mL, 0.018 mmoL) were dissolved in ethanol (3 mL) and heated at reflux. It was then treated with a solution of potassium hydroxide (0.0012 g, 0.019 mmoL) dissolved in H2O (3 mL) by addition over 10 min. The reaction was refluxed for 1 hr then it was concentrated in vacuo. The residue was dissolved in diethyl ether (50 mL) and washed with brine (1×50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, ethyl acetate:hexanes (25:75)) to afford 1.97 g (44%) of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 6.74-6.92 (m, 8H) 4.57 (s, 1H) 4.40-4.51 (m, 1H) 1.32 (d, J=5.88 Hz, 6H). MS m/z (DCI) 266 (M+NH4)+.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe reaction was refluxed for 1 hr
  4. concentrationit was concentrated in vacuo
  5. dissolutionThe residue was dissolved in diethyl ether (50 mL)
  6. washwashed with brine (1×50 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography (SiO2, ethyl acetate:hexanes (25:75))

Sources & evidence

ORD record
ord-67e08ff22ec84922ba151c15eebde084
Source dataset
uspto-grants-2012_06
Patent number
US08207350B2

Reaction notes

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