4-Isopropylphenol → HCID 23036319, compound

HRID 1709866Notes

Reaction equation

HRID 1709866 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 74654-IsopropylphenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 23036319HCID 23036319, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 27.4 g (0.2 mole) of p-isopropylphenol, 63 g (0.4 mole) of 1-bromo-3-chloropropane and 82.9 g (0.6 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 24 hr. The reaction mixture was cooled, filtered and filtrate concentrated. The residue was dissolved in 200 ml of benzene and treated with potassium hydroxide pellets to remove excess starting phenol. The mixture was stirred in ambient temperature for 0.5 hr, filtered through Celite® and the filtrate concentrated to give 36.4 g (87% yield) of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationfiltrate concentrated
  6. dissolutionThe residue was dissolved in 200 ml of benzene
  7. additiontreated with potassium hydroxide pellets
  8. customto remove excess starting phenol
  9. filtrationfiltered through Celite®
  10. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-13caa65a12e34dac90e7b717ea09b613
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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