Potassium Iodide → HCID 131711339, compound

HRID 1704113Notes

Reaction equation

HRID 1704113 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([Cl:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[I-].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>O1CCCC1.ClCCl.C(O)(=O)C>[CH3:22][O:21][C:19](=[O:20])[CH:18]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][C:7]=1[Cl:12])[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 73804-tert-Butyl-2-chlorophenolHCID 24758Sodium hydrideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711339HCID 131711339, compoundYield 96.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4.25 g of 4-tert.-butyl-2-chlorophenol, 30 ml of tetrahydrofuran and 0.88 g of sodium hydride (60% dispersion in oil) is stirred at room temperature for 1 hour. To the mixture is added 3.48 g of potassium iodide and then a solution of 8.28 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate in 30 ml of tetrahydrofuran is added dropwise. After stirring and heating in an oil bath at 60° C. for 18 hours, the mixture is poured into ice-water containing 3 ml of acetic acid. The mixture is extracted with ethyl acetate and the combined extracts washed with sodium bicarbonate solution, 10% sodium bisulfite and saturated sodium chloride solution. The dried (MgSO4) extract is concentrated under reduced pressure to give an amber gum. The gum is dissolved in dichloromethane and the solution passed through a column of silica gel with dichloromethane as eluent. From the main cuts there is obtained 10 g of product as a viscous oil.

Workup

  1. stirringAfter stirring
  2. temperatureheating in an oil bath at 60° C. for 18 hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe combined extracts washed with sodium bicarbonate solution, 10% sodium bisulfite and saturated sodium chloride solution
  5. dry with materialThe dried (MgSO4)
  6. extractionextract
  7. concentrationis concentrated under reduced pressure
  8. customto give an amber gum

Sources & evidence

ORD record
ord-ff79bf159dcb4839ab6a92588159cd64
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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