2,5-Dimethylphenol → Methallyl 2,5-dimethylphenyl ether

HRID 1780612Notes

Reaction equation

HRID 1780612 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]([CH3:20])=[CH2:19]>CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:19][C:18](=[CH2:17])[CH3:20]

Participants

5

Reactant 3

HCID 72672,5-DimethylphenolHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 19047064Methallyl 2,5-dimethylphenyl ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution 122.2 g of 2,5-dimethylphenol in 300 ml of acetone was added 83 g of anhydrous potassium carbonate and 150 ml of 3-chloro-2-methylpropene. After refluxing for 65 hours, the reaction mixture was filtered and concentrated under reduced pressure and diluted with 200 ml diethyl ether. The mixture was washed three times with 100 ml of 10% aqueous solution of sodium hydroxide. The combined organic extracts were washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under the reduced pressure to afford 168 g of methallyl 2,5-dimethylphenyl ether as colorless oil.

Workup

  1. temperatureAfter refluxing for 65 hours
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with 200 ml diethyl ether
  5. washThe mixture was washed three times with 100 ml of 10% aqueous solution of sodium hydroxide
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-0eac796b4a1a4869a4b77e9702ff3f0a
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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