Acetone → Benzene, 1,2,5-trimethyl-3-[(2-methyl-2-propenyl)oxy]-

HRID 1780599Notes

Reaction equation

HRID 1780599 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[C:11](=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]([CH3:20])=O>>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[O:10][CH2:17][C:18](=[CH2:20])[CH3:11]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 127692,3,5-Trimethylphenol

Product 1

HCID 11830229Benzene, 1,2,5-trimethyl-3-[(2-methyl-2-propenyl)oxy]-Yield 75%

Procedure

To a solution of 100 g of 2,3,5-trimethylphenol in 500 ml of acetone was added 75 g of anhydrous potassium carbonate. After refluxing for 45 hours, the reaction mixture was filtered, concentrated under reduced pressure and diluted with diethyl ether. The mixture was extracted three times with 300 ml of 20% 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 the compound of methallyl 2,3,5-trimethylphenyl ether(105 g, yield 75%) as colorless liquid.

Workup

  1. temperatureAfter refluxing for 45 hours
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with diethyl ether
  5. extractionThe mixture was extracted three times with 300 ml of 20% 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-f9193d2ce6844b489ec729db168068b3
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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