Acetone → 2,6-Diallyl4-benzyloxyphenol

HRID 1727291Notes

Reaction equation

HRID 1727291 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C([O-])([O-])=O.[K+].[K+].[CH3:26][C:27]([CH3:29])=O>>[CH2:16]([C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[C:13]([CH2:29][CH:27]=[CH2:26])[C:12]=1[OH:15])[CH:17]=[CH2:18]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7638MonobenzoneHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 219859512,6-Diallyl4-benzyloxyphenol

Procedure

To a solution of starting 4-benzyloxyphenol (20 g) in acetone (800 mL) were added allylbromide (50 mL) and K2CO3 (60 g). The reaction mixture was refluxed overnight. After cooling to the room temperature, the insoluble materials were removed by filtration. The filtrate was concentrated in vac. The residue was partitioned between ethyl ether (500 mL) and 2N aqueous NaOH (200 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vac. to give the desired product.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customthe insoluble materials were removed by filtration
  3. concentrationThe filtrate was concentrated in vac
  4. customThe residue was partitioned between ethyl ether (500 mL) and 2N aqueous NaOH (200 mL)
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vac

Sources & evidence

ORD record
ord-7db7d11367db4196b7ba4f3b41e230f5
Source dataset
uspto-grants-2009_02
Patent number
US07495020B2

Reaction notes

Loading…