Hydroquinone → 4-Isopropoxyphenol

HRID 404878Notes

Reaction equation

HRID 404878 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-].[Na+]>C(O)C.O.[OH-].[K+]>[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

7

Reactant 3

HCID 785HydroquinoneHCID 6362Isopropyl iodideHCID 14798Sodium Hydroxide

Product 1

HCID 820014-IsopropoxyphenolYield 46,969.801%

Reagents, catalysts & solvents 3

HCID 14797Potassium HydroxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of hydroquinone (20.0 g, 0.182 mmol) and 2-iodopropane (30.9 g, 0.182 mmol) in ethanol (25 mL) at refluxing was added KOH (88%, 12.2 mg, 0.191 mmol) in water (30 mL) over a period of 60 minutes. The resulting mixture was refluxed for 3 hours. The mixture was poured into 1N NaOH and extracted with ether (1×). The aqueous layer was acidified with 10% HCl to pH ˜5 and extracted with ether (2×). The combined extracts were washed with brine, dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate:hexane (1:8) to provide the title compound (13.01 g, 47.0%).

Workup

  1. temperatureat refluxing
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. extractionextracted with ether (1×)
  4. extractionextracted with ether (2×)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel eluting with ethyl acetate:hexane (1:8)

Sources & evidence

ORD record
ord-2ad708501fb643e2bae60f5625263073
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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