Propofol → 2,6-Diisopropylanisole

HRID 1386965Notes

Reaction equation

HRID 1386965 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].[C:14](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[O:13][CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 4943PropofolHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 6009752,6-DiisopropylanisoleYield 72.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,6-diisopropyl phenol (20 g, 0.11 mol), potassium carbonate (62 g, 0.45 mol), acetone (160 ml) and methyl iodide (28 ml, 0.45 mole) is refluxed for three days. The reaction mixture is filtered through celite, evaporated, dissolved in ether, washed twice with 1M sodium hydroxide, dried over magnesium sulphate and concentrated to afford 15.1 g (0.08 mol, 70%) of 2,6-diisopropyl anisole as a slightly yellow oil.

Workup

  1. temperatureis refluxed for three days
  2. filtrationThe reaction mixture is filtered through celite
  3. customevaporated
  4. dissolutiondissolved in ether
  5. washwashed twice with 1M sodium hydroxide
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1f6add6f653b4925b9969c9eb58db831
Source dataset
uspto-grants-2001_07
Patent number
US06266622B1

Reaction notes

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