Allyl bromide → Allyl 3,5-dimethylphenyl ether
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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 3 000 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
- temperatureThe mixture was refluxed for 18 hours
- temperaturecooled
- filtrationThe potassium carbonate was filtered off
- additionthe filtrate was treated with 3 000 ml of water
- extractionIt was extracted three times
- washwashed twice
- dry with materialThe organic phase was dried over potassium carbonate
- filtrationfiltered
- concentrationthe filtrate was concentrated
- 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
- customwere obtained
Sources & evidence
- ORD record
- ord-dbb53cdfa9aa49e5afdd276c75ff3e60
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06746990B2
Reaction notes
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