Hydroquinone → HCID 19894591, compound

HRID 217550Notes

Reaction equation

HRID 217550 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[K+]>CO>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 123681,6-DibromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 19894591HCID 19894591, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As expressed in the following reaction scheme, hydroquinone (1) (4.5 g) and 1,6-dibromo hexane (2) (10 g) were dissolved in methanol (100 ml) at room temperature. Adding potassium hydroxide (2.3 g) to the mixture solution, the resulting solution was refluxed at 60° C. overnight. Then, after lowering the solution to room temperature and evaporating methanol, the product was extracted three times with water (100 ml) and ethyl acetate (100 ml). After removing water with magnesium sulfate and evaporating the solvent, the product was refined by column chromatography (eluent: ethyl acetate/hexane=1/5) thereby obtaining 4.4 g of 4-(6-bromohexyloxy)phenol (3).

Workup

  1. customto room temperature
  2. customevaporating methanol
  3. extractionthe product was extracted three times with water (100 ml) and ethyl acetate (100 ml)
  4. customAfter removing water with magnesium sulfate
  5. customevaporating the solvent

Sources & evidence

ORD record
ord-b33c1944e73b4062a3086a6de20c49b5
Source dataset
uspto-grants-2012_06
Patent number
US08197708B2

Reaction notes

Loading…