4-Iodophenol → 1-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene

HRID 847171Notes

Reaction equation

HRID 847171 reaction equation
Cl[C:2]([CH3:6])([CH3:5])[C:3]#[CH:4].[I:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH3:5][C:2]([O:14][C:11]1[CH:12]=[CH:13][C:8]([I:7])=[CH:9][CH:10]=1)([CH3:6])[C:3]#[CH:4]

Participants

7

Reactant 3

HCID 108944-IodophenolHCID 14798Sodium HydroxideHCID 706791-Butyne, 3-chloro-3-methyl-

Product 1

HCID 149335571-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzeneYield 30%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloro-3-methyl-1-butyne (10.0 g, 97.9 mmol), 4-iodophenol (15.0 g, 68.4 mmol), sodium hydroxide (3.90 g, 97.5 mmol) and tetrabutylammonium hydrogen sulfate (9.33 g, 27.5 mmol) in methylene chloride (50 mL) and water (50 mL) was stirred for 19 days at room temperature. After separating the two layers, the organic layer was washed with 1 N sodium hydroxide followed by water, dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed successively with 1 N hydrochloric acid, 1 N sodium hydroxide, water, brine and dried over anhydrous magnesium sulfate. After removing drying agent, the solvent was removed in vacuo. The crude product was purified by flash chromatography on silica gel eluting with toluene/hexane (1:10) to give the title compound as an oil (5.78 g, 20.2 mmol) in 30% yield: 1H NMR (CDCl3) δ 7.56 (d, J=8.7 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 2.56 (s, 1H), 1.63 (s, 6H); 13C NMR (CDCl3) δ 155.4, 137.8, 123.5, 86.0, 85.6, 74.3, 72 6, 29.5.

Workup

  1. customAfter separating the two layers
  2. washthe organic layer was washed with 1 N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed successively with 1 N hydrochloric acid, 1 N sodium hydroxide, water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removing
  9. customdrying agent
  10. customthe solvent was removed in vacuo
  11. customThe crude product was purified by flash chromatography on silica gel eluting with toluene/hexane (1:10)

Sources & evidence

ORD record
ord-8b4f1d5ea1fe4a618110b36a9ef2daa6
Source dataset
uspto-grants-1992_08
Patent number
US05140031

Reaction notes

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