Allyl bromide → HCID 10921078, compound

HRID 1906665Notes

Reaction equation

HRID 1906665 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>C(OCC)C>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 10921078HCID 10921078, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(4-Hydroxyphenyl)ethanol (100 g), anhydrous potassium carbonate (100 g) and allyl bromide (98 g) were refluxed with stirring for 17 hours. The mixture was cooled, filtered (washing through with acetone) and evaporated under reduced pressure to give an oily residue. This residue was dissolved in diethyl ether, washed with aqueous sodium hydroxide, washed with saturated brine, dried (MgSO4) and evaporated in vacuo to afford an oil. This was chromatographed on a silica gel column using dichloromethane to afford 2-(4-allyloxyphenyl)ethanol (78 g).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. wash(washing through with acetone)
  4. customevaporated under reduced pressure
  5. customto give an oily residue
  6. washwashed with aqueous sodium hydroxide
  7. washwashed with saturated brine
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customto afford an oil
  11. customThis was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-53c043811eb04fc79d3f19c5c16aef93
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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