Phenol → 2-Nitro-5-phenoxytoluene

HRID 1683278Notes

Reaction equation

HRID 1683278 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH3:8])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 27284182-Nitro-5-phenoxytolueneYield 14.2%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of 5-fluoro-2-nitrotoluene (9.8 g), phenol (11.89 g), potassium carbonate (12.22 g) and copper bronze (1.0 g) was boiled for 16 hours. After cooling to room temperature the mixture was extracted with boiling diethyl ether (2×500 ml) and the combined organic phases washed with aqueous 1N sodium hydroxide (6×100 ml) and water (3×100 ml). After drying (MgSO4), solvent was removed at reduced pressure and the residue column chromatographed (silica gel, hexane→5% diethyl ether/hexane eluant) to give 2-nitro-5-phenoxytoluene (2.06 g) as an oil.

Workup

  1. extractionwas extracted with boiling diethyl ether (2×500 ml)
  2. washthe combined organic phases washed with aqueous 1N sodium hydroxide (6×100 ml) and water (3×100 ml)
  3. dry with materialAfter drying (MgSO4), solvent
  4. customwas removed at reduced pressure
  5. customthe residue column chromatographed (silica gel, hexane→5% diethyl ether/hexane eluant)

Sources & evidence

ORD record
ord-ddbe286981bd4ad5bce891cc644e3038
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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