Hydroquinone → 4-(4-Methyl-2-nitrophenoxy)phenol

HRID 607230Notes

Reaction equation

HRID 607230 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C([O-])([O-])=O.[K+].[K+].F[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>CN(C=O)C.CCOC(C)=O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 1362874-Fluoro-3-nitrotoluene

Product 1

HCID 608710474-(4-Methyl-2-nitrophenoxy)phenol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of hydroquinone (3.2 g, 29.0 mmol) and K2CO3 (8.0 g, 54.0 mmol) in 40 mL of DMF was heated at 100° C. with 1-fluoro-4-methyl-2-nitrobenzene (3.0 g, 19.3 mmol) with stirring for 24 hours. Cooled to room temperature and diluted with EtOAc. Washed with water and dried the organic layer over MgSO4. Filtered and concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 5% EtOAc/hexane giving an orange oil (1.89 g, 40%).

Workup

  1. washWashed with water
  2. dry with materialdried the organic layer over MgSO4
  3. filtrationFiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6445831d968c4223a98ecdaefe1eca18
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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