Potassium Iodide → HCID 131711331, compound

HRID 1704102Notes

Reaction equation

HRID 1704102 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][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19]>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[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][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711331HCID 131711331, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

As described in Example 30, a mixture of 3.13 g of p-tert.-butylphenol, 0.755 g of 60% sodium hydride-oil dispersion, 3.5 g of potassium iodide, one ml of hexamethylphosphoramide and 7.9 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate in 70 ml of tetrahydrofuran is refluxed for 18 hours and worked-up to give 9.0 g of an oil. The oil is chromatographed over silica gel with dichloromethane as eluent to give 7.4 g of oil which is crystallized from petroleum ether-ether to give 5.7 g of white crystals, mp 98°-101° C.

Workup

  1. temperatureis refluxed for 18 hours

Sources & evidence

ORD record
ord-03499f8ad2884687a68074c121ab8ac7
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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