2-Tert-Butylphenol → HCID 637356, compound

HRID 1756689Notes

Reaction equation

HRID 1756689 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CC(C)=O.C(OCC)(=O)C>[CH2:20]([O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:2]([CH3:1])([CH3:3])[CH3:4])[CH:19]=[CH2:18]

Participants

6

Reactant 3

HCID 69232-Tert-ButylphenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 637356HCID 637356, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 150 g (1 mol) of 2-(1,1-dimethylethyl)phenol, 151.8 g (1.1. mol) of potassium carbonate and 115 g (1.05 mol) of allyl bromide dissolved in 500 ml of acetone was stirred at reflux temperature for 70 hours and then cooled to room temperature. Once cooled, all precipitates were removed by filtration and the resulting filtrate was concentrated to provide a residue. This residue was dissolved in ethyl acetate and the resulting solution was washed with a 1 N hydrochloric acid solution, water and then a saturated brine solution and then concentrated to dryness to provide a residue. This residue was purified by column chromatography, using hexane as eluent, to provide 167.1 g of title compound.

Workup

  1. temperatureat reflux temperature for 70 hours
  2. temperatureOnce cooled
  3. customall precipitates were removed by filtration
  4. concentrationthe resulting filtrate was concentrated
  5. customto provide a residue
  6. washthe resulting solution was washed with a 1 N hydrochloric acid solution, water
  7. concentrationa saturated brine solution and then concentrated to dryness
  8. customto provide a residue
  9. customThis residue was purified by column chromatography

Sources & evidence

ORD record
ord-44ed9887012045cb996f396c4da09986
Source dataset
uspto-grants-1995_08
Patent number
US05441984

Reaction notes

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