Water → 2-(1,1-Dimethylethyl)phenoxypropene

HRID 273890Notes

Reaction equation

HRID 273890 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:7][C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH:1]=[CH:2][CH3:3])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 69232-Tert-ButylphenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 676312242-(1,1-Dimethylethyl)phenoxypropene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

Allyl bromide (69.2 ml), 2-t-butylphenol (122.9 ml) and potassium carbonate (121.6 g) were stirred in 265 ml of acetone at reflux temperature for 50 hours and then cooled to 35° C. Water (600 ml) was added and the resulting layers were separated. The aqueous layer was extracted with 600 ml of diethyl ether. The organic layer was combined with the aqueous layer's ether extract and the resulting solution was dried over sodium sulfate overnight. After sodium sulfate removal, the solvent was evaporated to provide, after further workup, 147 g of the subtitled intermediate.

Workup

  1. temperatureat reflux temperature for 50 hours
  2. customthe resulting layers were separated
  3. extractionThe aqueous layer was extracted with 600 ml of diethyl ether
  4. extractionextract
  5. dry with materialthe resulting solution was dried over sodium sulfate overnight
  6. customAfter sodium sulfate removal
  7. customthe solvent was evaporated
  8. customto provide

Sources & evidence

ORD record
ord-13c39daa9ec4453d8df37db31bf72c75
Source dataset
uspto-grants-1995_02
Patent number
US05387690

Reaction notes

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