Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 1645950Notes

Reaction equation

HRID 1645950 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. 7/8 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. 7/8 0.03 mm Hg)

Sources & evidence

ORD record
ord-3545e9ee4c7e4399802033d2e66ed5cf
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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