Sodium Iodide → HCID 23370065, compound

HRID 1901071Notes

Reaction equation

HRID 1901071 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1.[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29])([O-:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 1900717Phenol, 4-(3-bromopropyl)-2,6-bis(1,1-dimethylethyl)-

Product 1

HCID 23370065HCID 23370065, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-bromopropyl)-2,6-di-t-butylphenol (1.20 g), 2-nitrophenol (0.51 g), potassium carbonate (1.01 g) and a catalytic amount of sodium iodide was stirred in dimethylformamide (10 ml) at 60°-70° C. for 1.5 hrs. The reaction solution was poured into water, extracted with ethyl acetate, washed with water and then saturated saline, and dried over anhydrous MgSO4. After distilling off the solvent, the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=10:1) to give 4-[3-(2-nitrophenoxy)propyl]-2,6-di-t-butylphenol (1.05 g, 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialsaturated saline, and dried over anhydrous MgSO4
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a1d008a519fd43189374a7c16e7ebb55
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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