3,4,5-Trimethylphenol → Methallyl 3,4,5-trimethylphenyl ether

HRID 1780607Notes

Reaction equation

HRID 1780607 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH3:9])[C:7]=1[CH3:8].Cl[CH2:12][C:13]([CH3:15])=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([O:10][CH2:14][C:13](=[CH2:12])[CH3:15])[CH:5]=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 106963,4,5-TrimethylphenolHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 19047072Methallyl 3,4,5-trimethylphenyl ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution 20 g of 3,4,5-trimethylphenol in 150 ml of absolute acetone was added 22 ml of 3-chloro-2-methylpropene and 20.3 g of anhydrous potassium carbonate. After refluxing for 45 hours, the reaction mixture was filtered, washed with acetone, concentrated under reduced pressure and diluted with 200 ml of diethyl ether. The mixture was extracted three times with 50 ml of 2N hydrochloric acid and 50 ml of 20% aqueous solution of sodium hydroxide. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under the reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 27 g of methallyl 3,4,5-trimethylphenyl ether as yellow oil.

Workup

  1. temperatureAfter refluxing for 45 hours
  2. filtrationthe reaction mixture was filtered
  3. washwashed with acetone
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with 200 ml of diethyl ether
  6. extractionThe mixture was extracted three times with 50 ml of 2N hydrochloric acid and 50 ml of 20% aqueous solution of sodium hydroxide
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under the reduced pressure
  11. customto afford a crude product
  12. customFinal purification

Sources & evidence

ORD record
ord-c1ec75963aea46ea968458eb4ba5b3bb
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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