Water → Methyl 4-(allyloxy)benzoate

HRID 742519Notes

Reaction equation

HRID 742519 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20].O>CC(C)=O>[CH2:20]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 4645407Methyl 4-(allyloxy)benzoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 15.0 g (98.6 mmol) of methyl p-hydroxybenzoate and 13.0 g (94.1 mmol) of potassium carbonate mixed in 150 ml of acetone were added 13 ml (150 mmol) of allyl bromide and the whole was stirred at 80° C. for 2 hours under an argon gas atmosphere. Water was added to the solution and the whole was extracted with ethyl acetate. Then, the organic phase was washed with 5% aqueous solution of sodium hydroxide and saturated saline solution. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 18.6 g of methyl p-allyloxybenzoate (11) (yield: 96.6%).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThen, the organic phase was washed with 5% aqueous solution of sodium hydroxide and saturated saline solution
  3. customAfter removal of the solvent
  4. distillationby distillation
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e655ff874cc74f999741141cc4f86a4b
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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