2-Naphthol → Naphthalene, 2-(2-nitrophenoxy)-

HRID 1737221Notes

Reaction equation

HRID 1737221 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>O1CCCC1>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 86632-NaphtholHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 9280487Naphthalene, 2-(2-nitrophenoxy)-Yield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-hydroxynaphthalene (5 g, 34.7 mmol) in anhydrous tetrahydrofuran was added 2-fluoronitrobenzene (4.90 g, 34.7 mmol) at room temperature. The resultant mixture was heated at reflux overnight. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, the residue was diluted with water, the resulting mixture was extracted twice with methylene chloride and the combined extracts were dried (MgSO4). The resultant organic layer was concentrated under reduced pressure to yield 9.2 g of the title compound of Step A as an oil. Rf 0.45 (silica gel, 4:1 hexane-ethyl acetate).

Workup

  1. temperatureat reflux overnight
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionthe resulting mixture was extracted twice with methylene chloride
  5. dry with materialthe combined extracts were dried (MgSO4)
  6. concentrationThe resultant organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6006c8c328c44bcea5b53027a34b0c78
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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