Allyl bromide → Allyl 3,5-dimethylphenyl ether

HRID 1886215Notes

Reaction equation

HRID 1886215 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH2:12][CH:11]=[CH2:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 79483,5-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 257959Allyl 3,5-dimethylphenyl etherYield 104.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

46.73 g (383 mmol) of 3,5-dimethylphenol (Compound No. 1) was dissolved in 100 ml of methyl ethyl ketone. To this solution, 55.6 g (460 mmol) of allyl bromide and 79.3 g (575 mmol) of anhydrous potassium carbonate were added. The thus obtained mixture was refluxed overnight under an argon atmosphere. The reaction mixture was then extracted with hexane. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated, whereby 65.0 g of a crude 3,5-dimethyl-1-(2-propenyloxy)benzene (Compound No. 2) was obtained as a colorless oil.

Workup

  1. temperatureThe thus obtained mixture was refluxed overnight under an argon atmosphere
  2. extractionThe reaction mixture was then extracted with hexane
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f423a4ea871f4d219a6c5f6c55b183e5
Source dataset
uspto-grants-1992_09
Patent number
US05149834

Reaction notes

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