Allyl bromide → HCID 22718066, compound

HRID 460446Notes

Reaction equation

HRID 460446 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][CH2:22][CH:21]=[CH2:20])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2886346-Methoxy-2-naphthol

Product 1

HCID 22718066HCID 22718066, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-Methoxy-2-naphthol (22.1 g, 127.0 mmol) was dissolved in acetone (200 ml). Potassium carbonate (70.2 g, 508.0 mmol) and allyl bromide (16.5 ml, 191.0 mmol) were added to the resulting solution followed by stirring for 2 days at room temperature. After the reaction mixture was filtered, the organic solvent was distilled off under reduced pressure. Water was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The organic solvent was distilled off again to give 6-methoxy-2-(2-propenyloxy)naphthalene (24.9 g, Yield 91%) as a crude product.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. distillationthe organic solvent was distilled off under reduced pressure
  3. additionWater was added to the residue, which
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe organic solvent was distilled off again

Sources & evidence

ORD record
ord-190279e52d5e43c99f140d56b0a8246c
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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