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

HRID 2197837Notes

Reaction equation

HRID 2197837 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-4836bc5a95824295b8c6513f6543a814
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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