Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 1492588Notes

Reaction equation

HRID 1492588 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 4645407Methyl 4-(allyloxy)benzoateYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 2 L flask was equipped with a mechanical stirrer, a reflux condenser and a stopper, then charged with 50.05 g (0.329 mol) of methyl 4-hydroxybenzoate, 960 mL of acetone, 22.50 g (1.625 mol) of anhydrous potassium carbonate, 80.5 mL (112.6 g, 0.932 mol) of allyl bromide and the mixture was stirred and refluxed for 14 hours. The mixture was cooled to room temperature, filtered and concentrated to an oil. The residual oil was purified by distillation (97° C. @0.03 mm Hg) to afford 53.52 g (86%) of the title compound.

Workup

  1. customA 2 L flask was equipped with a mechanical stirrer, a reflux condenser
  2. temperaturerefluxed for 14 hours
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. distillationThe residual oil was purified by distillation (97° C. @0.03 mm Hg)

Sources & evidence

ORD record
ord-619f1aa087e44ec197ba02495ecc6f3f
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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