Allyl bromide → Ethyl 4-(prop-2-en-1-yloxy)benzoate

HRID 1603895Notes

Reaction equation

HRID 1603895 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 227685Ethyl 4-(prop-2-en-1-yloxy)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 4-hydroxybenzoate (10.0 g, 60.2 mmol) and potassium carbonate (8.32 g, 60.2 mmol) in acetone (50 ml) was added with allyl bromide (7.22 ml, 66.2 mmol) and the mixture was refluxed for 18 h. After that potassium carbonate was filtered off and the solvent was evaporated under reduced pressure, thereby obtaining 12.3 g of a crude containing only the title compound (99% yield).

Workup

  1. temperaturethe mixture was refluxed for 18 h
  2. filtrationAfter that potassium carbonate was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customobtaining 12.3 g of a crude

Sources & evidence

ORD record
ord-e1718fa357a349769b01f175598e27a4
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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