Potassium Iodide → HCID 131711325, compound

HRID 1704088Notes

Reaction equation

HRID 1704088 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=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][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19]>O1CCCC1.C(O)(=O)C.O.CN(C)P(N(C)C)(N(C)C)=O>[CH3:21][O:20][C:18](=[O:19])[CH:17]([O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 24758Sodium hydrideHCID 54271297HCID 54271297, compound

Product 1

HCID 131711325HCID 131711325, compoundYield 117.1%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 3.3 g of 3-tert.-butylphenol and 0.83 g of 60% sodium hydride-oil dispersion in 40 ml of tetrahydrofuran is stirred under argon for 1 hour at room temperature. To the mixture is added 3.65 g of potassium iodide, one ml of hexamethylphosphoramide and dropwise, a solution of 8.51 g of methyl bromo{p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 30 ml of tetrahydrofuran. The mixture is refluxed for 18 hours and poured into 500 ml of water containing 2 ml of acetic acid. The mixture is extracted with ether and the ether extracts washed with sodium bicarbonate solution, 10% sodium bisulfite solution and with saturated sodium chloride solution. The solvent is removed under reduced pressure to give 11.7 g of a gum. Chromatography over silica gel with dichloromethane as eluent gives 6 g of product as a gum.

Workup

  1. temperatureThe mixture is refluxed for 18 hours
  2. extractionThe mixture is extracted with ether
  3. washthe ether extracts washed with sodium bicarbonate solution, 10% sodium bisulfite solution and with saturated sodium chloride solution
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-dc40c9a210f14210b3fe22acd235f9a1
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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