Hydroquinone → 4-Isopropoxyphenol

HRID 1773959Notes

Reaction equation

HRID 1773959 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].I[CH:10]([CH3:12])[CH3:11].[OH-].[K+]>CCO.O>[CH:10]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 6362Isopropyl iodideHCID 14797Potassium Hydroxide

Product 1

HCID 820014-Isopropoxyphenol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of hydroquinone (3.37 g, 30.0 mmol, 1.00 eq.) and 2-iodopropane (2 mL, 19.8 mmol, 0.66 eq.) in EtOH (12 mL), a solution of KOH (1.68 g, 30.0 mmol, 1.00 eq.) in water (6 mL) was added. The dark brown solution was refluxed for 18 hours. The solvent was removed in vacuo and the remaining aq. phase was acidified with 2M aq. HCl soln. and extracted with AcOEt (3×15 mL). The comb. org. layers were washed with sat. aq. NaCl soln., dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 340 g, flow: 90 mL/min, 100 fractions of 45 mL, Heptane to Heptane+35% AcOEt) to yield 4-isopropoxy-phenol as an orange oil.

Workup

  1. temperatureThe dark brown solution was refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. extractionand extracted with AcOEt (3×15 mL)
  4. washlayers were washed with sat. aq. NaCl soln
  5. dry with material, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flashmaster (column: 340 g, flow: 90 mL/min, 100 fractions of 45 mL, Heptane to Heptane+35% AcOEt)

Sources & evidence

ORD record
ord-d4af45f3ca92475bbb5f3e8adacb9fcd
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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