Phenol → 1-Nitro-4-phenoxybenzene

HRID 365378Notes

Reaction equation

HRID 365378 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCC.[H-].[Na+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1>CS(C)=O>[CH:4]1[CH:5]=[CH:6][C:1]([O:7][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 8058HexaneHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 121101-Nitro-4-phenoxybenzeneYield 91.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

Phenol (1.89 g, 20 mmol) was added to a slurry of hexane-washed NaH (60% oil suspension, 820 mg, 20.5 mmol) in DMSO (20 mL), stirred under nitrogen at 20° C., producing strong gas evolution. After 30 minutes, 1-fluoro-4-nitrobenzene (2.82 g, 20 mmol) was added dropwise to the light grey slurry. After about 10 minutes, the reaction mixture became orange and quite strongly exothermic, and a lot of gas was evolved. After 2 hours, the reaction mixture was poured onto ice-water (200 mL), and the solid was collected by Buchner filtration, rinsed with water (2×50 mL), and air dried to give 4-nitrodiphenyl ether (3.945 g, 91.6%) as dull yellow crystals.

Workup

  1. customproducing strong gas evolution
  2. waitAfter about 10 minutes
  3. waitAfter 2 hours
  4. additionthe reaction mixture was poured onto ice-water (200 mL)
  5. filtrationthe solid was collected by Buchner filtration
  6. washrinsed with water (2×50 mL), and air
  7. customdried

Sources & evidence

ORD record
ord-c251f7d8564a4ca298fdf6b9bde7cd24
Source dataset
uspto-grants-2000_10
Patent number
US06127374

Reaction notes

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