Hydroquinone → 4-[(But-3-en-1-yl)oxy]phenol

HRID 859807Notes

Reaction equation

HRID 859807 reaction equation
[OH-].[K+].[C:3]1([CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[OH:4].Br[CH2:12][CH2:13][CH:14]=[CH2:15]>C(O)C>[CH2:15]([O:4][C:3]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[CH2:14][CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 21241Homoallyl bromide

Product 1

HCID 539866614-[(But-3-en-1-yl)oxy]phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a three-necked flask equipped with a dropping funnel, a mixture composed of potassium hydroxide (27 mmol) and hydroquinone (45 mmol) is dissolved in 400 ml of absolute ethanol by heating. Add 4-bromo-1-butene (Aldrich) (18 mmol) dropwise. Maintain at reflux for 4 hours. After being cooled and filtered the solvent is evaporated. The mixture is taken up in a solution of ice-cold water. That dissolves a part of the hydroquinone and leads to the appearance of a precipitate containing the desired product. Extract the product with ether. After three washings with water, the organic phase is dried over sodium sulfate then the solvent is evaporated. The phenyl is purified by chromatography on silica gel (eluent: heptane-ether 5/5). The yield of the reaction is of the order of 50%.

Workup

  1. customIn a three-necked flask equipped with a dropping funnel
  2. temperatureby heating
  3. temperatureMaintain
  4. temperatureat reflux for 4 hours
  5. temperatureAfter being cooled
  6. filtrationfiltered the solvent
  7. customis evaporated
  8. dissolutionThat dissolves a part of the hydroquinone
  9. additioncontaining the desired product
  10. extractionExtract the product with ether
  11. washAfter three washings with water
  12. dry with materialthe organic phase is dried over sodium sulfate
  13. customthe solvent is evaporated
  14. customThe phenyl is purified by chromatography on silica gel (eluent: heptane-ether 5/5)

Sources & evidence

ORD record
ord-275602f9da5c4e24b57095dbbc8b485b
Source dataset
uspto-grants-2006_12
Patent number
US07153517B2

Reaction notes

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