Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 2399504Notes

Reaction equation

HRID 2399504 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° [email protected] 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° [email protected] mm Hg)

Sources & evidence

ORD record
ord-d9c8267ffa034cdf95d7c8bc6599d87b
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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