4-Chlorophenol → HCID 131711330, compound

HRID 1704101Notes

Reaction equation

HRID 1704101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[I-].[K+].Br[CH:14]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16]>C(O)(=O)C.CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>[CH3:18][O:17][C:15](=[O:16])[CH:14]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711330HCID 131711330, compoundYield 95.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 2.57 g of p-chlorophenol, 0.72 g of 60% sodium hydride-oil dispersion and 25 ml of tetrahydrofuran is stirred at room temperature for 90 minutes. To the mixture under argon is added 3.32 g of potassium iodide, 1 ml of hexamethylphosphoramide, and dropwise a solution of 7.5 g of methyl bromo{p-[3-(p-chlorphenoxy)propoxy]phenyl}acetate. The mixture is stirred at room temperature for 1 hour and refluxed for 18 hours. The mixture is poured into 500 ml of ice-water containing 1.2 ml of acetic acid. The mixture is extracted with ether and the extracts washed with saturated sodium chloride solution and dried (MgSO4). The solvent is removed under reduced pressure to give 8.0 g of product as an oil. Chilling gives crystals. Recrystallization from 90% ethanol gives white crystals, mp 80°-82° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. temperaturerefluxed for 18 hours
  3. extractionThe mixture is extracted with ether
  4. washthe extracts washed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-09ee8daf2880454199ebf9b4063a4275
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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