Potassium Iodide → HCID 131711343, compound

HRID 1704124Notes

Reaction equation

HRID 1704124 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[I-].[K+].Br[CH:17]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:39])[CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19]>O1CCCC1.C(O)(=O)C>[CH3:21][O:20][C:18](=[O:19])[CH:17]([O:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH:29]([CH3:39])[CH2:30][O:31][C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 54515270HCID 54515270, compound

Product 1

HCID 131711343HCID 131711343, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 2.36 g of p-t-butylphenol in 3 ml of tetrahydrofuran is added 0.625 g of sodium hydride (60% dispersion in oil). After stirring under argon for 1 hour and heating at 50° C. for 20 minutes, 2.4 g of potassium iodide and 6.0 g of methyl bromo{p-[2-(p-chlorophenoxy)-1-methylethoxy]phenyl}acetate in 30 ml of tetrahydrofuran is added. The mixture is stirred and refluxed for 18 hours and poured into 300 ml of ice-water containing 3 ml of acetic acid. The mixture is extracted with dichloromethane and the extracts washed with saturated NaHCO3, 10% sodium thiosulfate and saturated sodium chloride solution. The dichloromethane extract is dried (MgSO4) and the solvent removed under reduced pressure to give 6.7 g of product as a gum. Chromatography over silica gel with dichloromethane as eluent gives 5.7 g of yellow gum.

Workup

  1. stirringThe mixture is stirred
  2. temperaturerefluxed for 18 hours
  3. extractionThe mixture is extracted with dichloromethane
  4. washthe extracts washed with saturated NaHCO3, 10% sodium thiosulfate and saturated sodium chloride solution
  5. extractionThe dichloromethane extract
  6. dry with materialis dried (MgSO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4a4b4883fcec4168991097e4ea161bcb
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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