Allyl bromide → Allyl 3,5-dimethylphenyl ether

HRID 277670Notes

Reaction equation

HRID 277670 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+]>CC(C)=O>[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

Procedure

1000 g of 3,5-dimethylphenol (A) were dissolved in 1000 ml of acetone, 980 g of allyl bromide were added dropwise, and 114.8 g of potassium carbonate were subsequently added. The mixture was refluxed for 18 hours and then cooled. The potassium carbonate was filtered off, and the filtrate was treated with 3000 ml of water. It was extracted three times using tert-butyl methyl ether, and the organic phases were combined and washed twice using in each case 300 ml of 10% strength sodium hydroxide solution. The organic phase was dried over potassium carbonate and filtered, and the filtrate was concentrated. After distillation, 837 g (64% of theory) of allyl 3,5-dimethylphenyl ether of a boiling point of 98 to 110° C. at 10 mbar were obtained.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled
  3. filtrationThe potassium carbonate was filtered off
  4. additionthe filtrate was treated with 3000 ml of water
  5. extractionIt was extracted three times
  6. washwashed twice
  7. dry with materialThe organic phase was dried over potassium carbonate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. distillationAfter distillation, 837 g (64% of theory) of allyl 3,5-dimethylphenyl ether of a boiling point of 98 to 110° C. at 10 mbar
  11. customwere obtained

Sources & evidence

ORD record
ord-74072ada2f9d4ccaa39515c72a09bc0b
Source dataset
uspto-grants-2002_03
Patent number
US06358887B1

Reaction notes

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