Potassium Iodide → HCID 131711326, compound

HRID 1704090Notes

Reaction equation

HRID 1704090 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[H-].[Na+].[I-].[K+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:19][O:18][C:16](=[O:17])[CH:15]([O:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 72493,4-DimethylphenolHCID 24758Sodium hydrideHCID 54271297HCID 54271297, compound

Product 1

HCID 131711326HCID 131711326, compoundYield 110.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 2.70 g of 3,4-dimethylphenol and 0.89 g of 60% sodium hydride-oil dispersion in 40 ml of tetrahydrofuran is stirred at room temperature for 1 hour. To the mixture is added 3.7 g of potassium iodide, 1 ml of hexamethylphosphoramide and dropwise a solution of 8.55 g of methyl bromo{p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 30 ml of tetrahydrofuran. The mixture is refluxed for 18 hours and worked-up as described in Example 5 to give 10.4 g of a gum. Chromatography over silica gel with dichloromethane as eluent gives the product as a gum.

Workup

  1. temperatureThe mixture is refluxed for 18 hours

Sources & evidence

ORD record
ord-e67b382ae3444732949087173caba151
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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