Acetone → Methyl 4-(allyloxy)benzoate

HRID 580966Notes

Reaction equation

HRID 580966 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.[CH3:18][C:19]([CH3:21])=O>C(Br)C=C>[CH2:21]([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7456MethylparabenHCID 11430Potassium Carbonate

Product 1

HCID 4645407Methyl 4-(allyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 7841Allyl bromideSolvent

Procedure

Anhydrous potassium carbonate (55 g) in acetone (400 ml) and allyl bromide (41.5 ml) were added to a stirred solution of methyl 4-hydroxybenzoate (60.8 g). The mixture was heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature, filtered and the residue washed with ethyl acetate. The filtrates and washings were combined, evaporated and the residue dissolved in dichloromethane. The organic phase was washed with 1M aqueous sodium hydroxide (2×75 ml), water, brine and dried (MgSO4). Evaporation gave methyl 4-allyloxybenzoate as an oil (76.4 g) which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. filtrationfiltered
  4. washthe residue washed with ethyl acetate
  5. customevaporated
  6. dissolutionthe residue dissolved in dichloromethane
  7. washThe organic phase was washed with 1M aqueous sodium hydroxide (2×75 ml), water, brine
  8. dry with materialdried (MgSO4)
  9. customEvaporation

Sources & evidence

ORD record
ord-3f55c95cdce04ae7810f971d43e49687
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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