Phenol → 2-Nitro-5-phenoxytoluene

HRID 1745

Reaction equation

HRID 1745 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([CH3:21])[CH:20]=1>CN(C)C(=O)C>[N+:22]([C:18]1[CH:17]=[CH:16][C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:20][C:19]=1[CH3:21])([O-:24])=[O:23]

Participants

5

Reactant 3

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

Product 1

HCID 27284182-Nitro-5-phenoxytoluene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
20 °C

Procedure

14.1 g (150 mmol) of phenol were dissolved in 120 ml of anhydrous N,N-dimethylacetamide, while stirring, 20.6 g (150 mmol) of finely powdered potassium carbonate were added and the mixture was stirred at 70°-80° C. for 30 minutes. After cooling to 20° C., 23.25 g (18.3 ml, 150 mmol) of 5-fluoro-2-nitrotoluene were added dropwise, the mixture was heated at 135°-140° C. for 2 hours and, after cooling, concentrated in vacuo, the residue was introduced into ice and the crystalline product was filtered off with suction, washed with water and dried, 30 g, melting point 43°-46° C.

Workup

  1. stirringthe mixture was stirred at 70°-80° C. for 30 minutes
  2. temperaturethe mixture was heated at 135°-140° C. for 2 hours
  3. temperatureafter cooling
  4. concentrationconcentrated in vacuo
  5. additionthe residue was introduced into ice
  6. filtrationthe crystalline product was filtered off with suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7ccd2207c11e4dc982df4da8ca022082
Source dataset
uspto-grants-1998_03
Patent number
US05726305

Linked notes

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