Hydrochloric Acid → 4-(4-Chloro-2-nitrophenoxy)phenol

HRID 607258Notes

Reaction equation

HRID 607258 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[K+].Cl[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].Cl>CS(C)=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 69772,5-DichloronitrobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 129406294-(4-Chloro-2-nitrophenoxy)phenolYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of hydroquinone (1.21 g, 0.011 mol) and potassium hydroxide (0.894 g, 0.0159 mol) in anhydrous dimethylsulfoxide (7 mL) was heated at 120° for 30 minutes under a nitrogen atmosphere. A solution of 2,5-dichloronitrobenzene (1.90 g, 0.0099 mol) in dimethylsulfoxide (3 mL) was added dropwise over a 30 minute period at 120° then let the reaction stir for 1 hour at the same temperature. The reaction was then cooled in an ice bath and poured into 30 mL of ice water. The mixture was acidified with concentrated hydrochloric acid to pH 1 and extracted with ethyl ether (2×50 mL). The combined ethereal extracts were washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. Purification of the residue by silica gel chromatography using methylene chloride as eluent provided the product as a tan solid (1.34 g, 51%).

Workup

  1. temperatureThe reaction was then cooled in an ice bath
  2. extractionextracted with ethyl ether (2×50 mL)
  3. washThe combined ethereal extracts were washed with water (3×150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation under vacuum
  7. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-ca046005057d4e9c89e43702e17e408e
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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