4-Chlorophenol → HCID 131711327, compound

HRID 1704091Notes

Reaction equation

HRID 1704091 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][O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:31][CH:30]=2)=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16]>O1CCCC1.C(O)(=O)C.CN(C)P(N(C)C)(N(C)C)=O>[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:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:33][CH:34]=2)=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 22761161HCID 22761161, compound

Product 1

HCID 131711327HCID 131711327, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 1.55 g of p-chlorophenol, 0.47 g of 60% sodium hydride-oil dispersion and 20 ml of tetrahydrofuran is stirred at room temperature for 90 minutes. To the mixture is added 2.22 g of potassium iodide, 1 ml of hexamethylphosphoramide and dropwise 5.04 g of methyl bromo{p-[2-(p-tert.-butylphenoxy)ethoxy]phenyl}acetate in 30 ml of tetrahydrofuran. The mixture is refluxed for 18 hours and poured into 350 ml of ice-water containing 1 ml of acetic acid. After stirring in an ice bath for 30 minutes, the mixture is filtered and the solid washed with water to give 5.5 g of product as tan crystals. Recrystallization by dissolving in acetone, adding hexane and distilling off the acetone gives 3.9 g of white crystals, mp 128°-130° C.

Workup

  1. temperatureThe mixture is refluxed for 18 hours
  2. stirringAfter stirring in an ice bath for 30 minutes
  3. filtrationthe mixture is filtered
  4. washthe solid washed with water

Sources & evidence

ORD record
ord-3850f21166084e2ca1ffb471cc5817a7
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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